Chemical compounds

ABSTRACT

The use of a compound of formula I 
     
       
         
         
             
             
         
       
     
     wherein
     X is (i), (ii) or (iii)   

     
       
         
         
             
             
         
       
         
         Y is O, S(O) m , NR 3 , CR 5 R 6 , CR 5 R 6 —CR 7 R 8 , O—CR 7 R 8 , S(O) m —CR 7 R 8 , NR 3 —CR 7 R 8 , CR 5 R 6 —O, CR 5 R 6 —S(O) m , CR 5 R 6 —NR 3 , SO 2 —NR 3 , NR 3 —SO 2 , NR 3 —O or O—NR 3 ; 
         m is 0, 1, or 2; 
         the ring (T) 
       
    
     
       
         
         
             
             
         
       
     
     is a 5- or 6-membered aromatic or heteroaromatic ring; R 1  to R 10  are specified organic groups and n and is 0, 1, 2, 3 or 4; or salts or N-oxides thereof or compositions containing them in controlling insects, acarines, nematodes or molluscs. Novel compounds are also provided.

This application is a divisional application of U.S. Ser. No.12/063,869, filed Jun. 16, 2008, which is a 371 of InternationalApplication No. PCT/GB2006/002886 filed Aug. 2, 2006, which claimspriority to GB 0516706.9 filed Aug. 15, 2005, the contents of which areincorporated herein by reference.

The present invention relates to thiazoline derivatives, to processesfor preparing them, to insecticidal, acaricidal, molluscicidal andnematicidal compositions comprising them and to methods of using them tocombat and control insect, acarine, mollusc and nematode pests.

Thiazoline derivatives with pharmaceutical properties are disclosed infor example in U.S. Pat. No. 3,636,219, IN 179230 and Coll. Czech Chem.Comm, 1992, 57, 415.

It has now surprisingly been found that certain thiazolines have goodinsecticidal properties.

The present invention therefore provides a method of combating andcontrolling insects, acarines, nematodes or molluscs which comprisesapplying to a pest, to a locus of a pest, or to a plant susceptible toattack by a pest an insecticidally, acaricidally, nematicidally ormolluscicidally effective amount of a compound of formula (I):

whereinX is (i), (ii) or (iii)

Y is O, S(O)_(m), NR³, CR⁵R⁶, CR⁵R⁶—CR⁷R⁸, O—CR⁷R⁸, S(O)_(m)—CR⁷R⁸,NR³—CR⁷R⁸, CR⁵R⁶—O, CR⁵R⁶—S(O)_(m), CR⁵R⁶—NR³, SO₂—NR³, NR³—SO₂, NR³—Oor O—NR³;m is 0, 1, or 2;the ring (T)

is a 5- or 6-membered aromatic or heteroaromatic ring;R¹, R², R⁵, R⁶, R⁷ and R⁸ are each independently H, OH, halogen, nitro,cyano, rhodano, carboxy, formyl, formyloxy, G-, G-O—, G-S—, G-A-,R²¹R²²N—, R²¹R²²N-A-, G-O-A-, G-S-A-, G-A-O—, G-A-S—, G-A-NR²³—,R²¹R²²N-A-O—, R²¹R²²N-A-S—, R²¹R²²N-A-NR²³—, G-O-A-O—, G-O-A-S—,G-O-A-NR²³—, G-S-A-O, G-S-A-NR²³—, or R²⁰S(O)(═NR¹⁷)—; or two of thegroups R¹, R², R⁵, R⁶, R⁷ and R⁸ attached to the same carbon atom are═O, ═S, ═NR¹¹ or ═CR¹²R¹³, or the groups R¹ and R², R⁵ and R⁶ or R⁷ andR⁸ together with the carbon atom to which they are attached form a threeto six membered ring, containing at least 2 carbon atoms and optionallycontaining one or two sulfur and/or one or two non-adjacent oxygen atomsor a group NR¹⁴, the ring being optionally substituted by C₁-C₆ alkyl;or two of the groups R¹, R², R⁵, R⁶, R⁷ and R⁸ attached to differentatoms together with the atoms they are attached form a three to sevenmembered ring, that optionally contains one or two sulfur and/or one ortwo non-adjacent oxygen atoms or a group NR¹⁴, the ring being optionallysubstituted by C₁-C₆ alkyl or two of the groups R¹, R², R⁵, R⁶, R⁷ andR⁸ attached to adjacent atoms combine to form a bond;R¹⁰ is H, OH, cyano, formyl, tri(C₁-C₆ alkyl)silyl, G-, G-O—, G-S—,G-S—S—, G-A-, R²⁴R²⁵N—, R²⁴R²⁵N—S—, R²⁴R²⁵N-A-, R¹⁸N═C(R¹⁹)—, G-A-NR⁶⁹—,R⁷⁰R⁷¹C═N—, G-O-A- or G-S-A-,R¹¹ is H, OH, nitro, cyano, formyl, formyloxy, G-, G-O—, G-A-, R³⁶R³⁷N—,G-C(O)—O—, G-C(O)—NR²⁶—, R³⁶R³⁷N—C(O)O—, G—OC(O)O—, G-OC(O)—NR²⁶—;R¹² and R¹³ are each independently H, halogen, nitro, cyano, formyl,formyloxy, G-, G-O—, G-S—, G-A-, R⁴⁰R⁴¹N—, R⁴⁰R⁴¹N-A-, G-O-A-, G-A-O—,R⁴⁰R⁴¹N-A-O—, R⁴⁰R⁴¹N-A-S—, G-O—A-O—, G-O-A-S—, G-O-A-NR³⁰—, or R¹² andR¹³ together with the carbon atom to which they are attached form a 3 to6 membered carbocyclic ring;R³, R¹⁴, R¹⁵ and R¹⁶ are each independently H, OH, cyano, formyl, G-,G-O—, G-S—, G-A-, R²⁷R²⁸N—, R²⁷R²⁸N-A-, G-O-A-, G-S-A-, G-A-NR²⁹—,R²⁷R²⁸NA-NR²⁹—, G-O-A-NR²⁹— or G-S-A-NR²⁹—;each R⁴ is independently OH, halogen, nitro, cyano, azido, rhodano,isothiocyanato, carboxy, formyl, formyloxy, G-, G-O—, G-S—, G-A-,R³¹R³²N—, R³¹R³²N-A-, G-O-A-, G-S-A-, G-A-O—, G-A-S—, G-A-NR³³—,R³¹R³²N-A-O—, R³¹R³²N-A-S—, R³¹R³²N-A-NR³³—, G-O-A-O—, G-O-A-S—, S—,G-O-A-NR³³—, G-S-A-O, G-S-A-NR³³—, R²⁰S(O)(═NR¹⁷)—, R¹⁸N═C(R¹⁹)—,R⁴⁴R⁴⁵P(O)— or R⁴⁴R⁴⁵P(S)—, or 2 adjacent groups R⁴ together with thecarbon atoms to which they are attached form a 4, 5, 6, or 7 memberedcarbocyclic or heterocyclic ring which may be optionally substituted byhalogen, or a group R⁴ together with a group R³, R⁵ or R⁹ and the atomsto which they are attached form a 5-7 membered ring optionallycontaining an NR¹⁵ group or an S or O atom, the ring being optionallysubstituted by C₁-C₆ alkyl;n is 0, 1, 2, 3 or 4;R⁹ is H, formyl, G, G-A-, R³⁴R³⁵N-A-, G-O-A- or G-S-A-, or R⁹ togetherwith a group R¹, R⁵ or R⁷ and the atoms to which they are attached mayform a three to seven membered ring, that optionally may contain one ortwo sulfur and/or one or two non-adjacent oxygen atoms or a group NR¹⁶;

R¹⁷ is H, G-, G-C(O)—, or G-OC(O)—;

R¹⁸ is H, OH, cyano, nitro, G-, G-O— or R³⁸R³⁹N—;R¹⁹ is H, cyano, G-, G-O—, G-S— or R⁴²R⁴³N—;R²⁰ is C₁₋₆ alkyl, optionally substituted phenyl, optionally substitutedbenzyl;each of the groups R²¹ to R⁴³ inclusive are independently H or G-, ortwo R²¹, R²², R²⁷, R²⁸, R³¹, R³², R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹, R⁴², R⁴³groups, together with the N atom to which they are attached, form agroup N═CR^(a)R^(b) (where R^(a) and R^(b) are H, or C₁₋₆ alkyl) or twoR²¹, R²², R²⁴, R²⁵, R²⁷, R²⁸, R³¹, R³², R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹,R⁴², R⁴³ groups, together with the N atom to which they are attached,form a five, six or seven-membered heterocyclic ring which may containone or two further heteroatoms selected from O, N or S and which may beoptionally substituted by one to four C₁₋₆ alkyl groups;R⁴⁴ and R⁴⁵ are independently C₁₋₆alkyl, C₁₋₆-alkoxy, phenyl, phenoxy;G is optionally substituted C₁₋₁₂ alkyl, optionally substituted C₂₋₁₂alkenyl, optionally substituted C₂₋₁₂ alkynyl, optionally substitutedC₃₋₈ cycloalkyl, optionally substituted C₃₋₈ cycloalkenyl, optionallysubstituted aryl, optionally substituted heteroaryl or optionallysubstituted heterocyclyl;

R⁶⁹ is H, G-, G-C(O)—, or G-OC(O)—;

R⁷⁰ and R⁷¹ are independently H, cyano, nitro, G-, G-O—, G-S—, or R⁷⁰and R⁷¹ together with the carbon atom to which they are attached form afive, six or seven-membered heterocyclic ring which may contain one ortwo further heteroatoms selected from O, N or S and which may beoptionally substituted by one to four C₁₋₆ alkyl groups;

A is S(O), SO₂, C(O) or C(S);

or salts or N-oxides thereof.

The compounds of formula (I) may exist in different geometric or opticalisomers or different tautomeric forms. One or more centres of chiralitymay be present, for example on the chiral carbon atoms CR¹R², CR⁵R⁶,CR⁷R⁸, CR⁹, or a chiral carbon unit in the group G, or a chiral —S(O)—unit, in which case compounds of the formula (I) may be present as pureenantiomers, mixtures of enantiomers, pure diastereomers or mixtures ofdiastereomers. There may be double bonds present in the molecule, suchas C═C or C═N bonds, in which case compounds of formula (I) may exist assingle isomers of mixtures of isomers. Centres of tautomerisation may bepresent. This invention covers all such isomers and tautomers andmixtures thereof in all proportions as well as isotopic forms such asdeuterated compounds.

The compounds of formula (I) contain an amidine moiety, which can existin two tautomeric forms when R¹⁰ is hydrogen. One of these formscontains an exocyclic C═N double bond, and one of them contains anendocyclic C═N double bond. When the C═N double bond is exocyclic thisdouble bond can exist in two geometric forms E and Z as shown by formula(I′) and (I″). Each form can be latentiated with a group R¹⁰. This groupR¹⁰ is selected to allow its removal by one or a combination ofbiochemical, chemical or physical processes to afford compounds offormula I where R¹⁰ is H before, during or following application to thetreated area or plants. Examples of these processes include enzymaticcleavage, chemical hydrolysis and photolysis. Compounds bearing groupsR¹⁰ may offer certain advantages, such as improved penetration of thecuticula of the plants treated, increased tolerance of crops, improvedcompatibility or stability in formulated mixtures containing otherherbicides, herbicide safeners, plant growth regulators, fungicides orinsecticides, increased movement in soils or reduced leaching in soils.

Suitable acid addition salts include those with an inorganic acid suchas hydrochloric, hydrobromic, sulfuric, nitric and phosphoric acids, oran organic carboxylic acid such as oxalic, tartaric, lactic, butyric,toluic, hexanoic and phthalic acids, or sulphonic acids such as methane,benzene and toluene sulphonic acids. Other examples of organiccarboxylic acids include haloacids such as trifluoroacetic acid.

N-oxides are oxidised forms of tertiary amines or oxidised forms ofnitrogen containing heteroaromatic compounds. They are described in manybooks for example in “Heterocyclic N-oxides” by Angelo Albini and SilvioPietra, CRC Press, Boca Raton, Fla., 1991.

Each alkyl moiety either alone or as part of a larger group (such as G,or alkoxy, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl) is a straight or branched chain and is, forexample, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl,iso-propyl, n-butyl, sec-butyl, iso-butyl, tert-butyl or neo-pentyl. Thealkyl groups are suitably C₁ to C₁₂ alkyl groups, but are preferablyC₁-C₁₀, more preferably C₁-C₈, even more preferably C₁-C₆ and mostpreferably C₁-C₄ alkyl groups.

The ring or chain forming alkylene, alkenylene and alkinylene groups canoptionally be further substituted by one or more halogen, C₁-C₃ alkyl,and/or C₁-C₃ alkoxy groups.

When present, the optional substituents on an alkyl moiety (alone or aspart of a larger group such as alkoxy, alkoxycarbonyl, alkylcarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl) include one or more ofhalogen, nitro, cyano, rhodano, isothiocyanato, C₃₋₇ cycloalkyl (itselfoptionally substituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl(itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy,C₁₋₁₀ alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy,tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy, C₁₋₆ alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀haloalkoxy, aryl(C₁₋₄)-alkoxy (where the aryl group is optionallysubstituted), C₃₋₇ cycloalkyloxy (where the cycloalkyl group isoptionally substituted with C₁₋₆ alkyl or halogen), C₂₋₁₀ alkenyloxy,C₂₋₁₀ alkynyloxy, SH, C₁₋₁₀ alkylthio, C₁₋₁₀ haloalkylthio,aryl(C₁₋₄)alkylthio (where the aryl group is optionally substituted),C₃₋₇ cycloalkylthio (where the cycloalkyl group is optionallysubstituted with C₁₋₆ alkyl or halogen),tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, arylthio (where the aryl group isoptionally substituted), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl,C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl (where the arylgroup may be optionally substituted), tri(C₁₋₄)alkylsilyl,aryldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl, triarylsilyl, formyl,C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆alkylaminocarbonyl, di(C₁₋₆ alkyl)aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₃alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, arylcarbonyloxy (where thearyl group is optionally substituted), di(C₁₋₆)alkylaminocarbonyloxy,oximes and oximethers such as ═NOalkyl, ═NOhaloalkyl and ═NOaryl (itselfoptionally substituted), aryl (itself optionally substituted),heteroaryl (itself optionally substituted), heterocyclyl (itselfoptionally substituted with C₁₋₆ alkyl or halogen), aryloxy (where thearyl group is optionally substituted), heteroaryloxy, (where theheteroaryl group is optionally substituted), heterocyclyloxy (where theheterocyclyl group is optionally substituted with C₁₋₆ alkyl orhalogen), amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆alkylcarbonylamino, N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino, C₂₋₆alkenylcarbonyl, C₂₋₆ alkynylcarbonyl, C₃₋₆ alkenyloxycarbonyl, C₃₋₆alkynyloxycarbonyl, aryloxycarbonyl (where the aryl group is optionallysubstituted) and arylcarbonyl (where the aryl group is optionallysubstituted).

Alkenyl and alkynyl moieties can be in the form of straight or branchedchains, and the alkenyl moieties, where appropriate, can be of eitherthe (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.Alkenyl and alkynyl moieties can contain one or more double and/ortriple bonds in any combination. It is understood, that allenyl andalkylinylalkenyl are included in these terms.

When present, the optional substituents on alkenyl or alkynyl includethose optional substituents given above for an alkyl moiety.

In the context of this specification acyl is optionally substituted C₁₋₆alkylcarbonyl (for example acetyl), optionally substituted C₂₋₆alkenylcarbonyl, optionally substituted C₃₋₆ cycloalkylcarbonyl (forexample cyclopropylcarbonyl, optionally substituted C₂₋₆alkynylcarbonyl, optionally substituted arylcarbonyl (for examplebenzoyl) or optionally substituted heteroarylcarbonyl.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups are alkyl groups which are substituted with one or moreof the same or different halogen atoms and are, for example, CF₃, CF₂Cl,CF₂H, CCl₂CH, FCH₂, ClCH₂, BrCH₂, CH₃CHF, CF₃CH₂ or CHF₂CH₂.

In the context of the present specification the terms “aryl”, “aromaticring” and “aromatic ring system” refer to ring systems which may bemono-, bi- or tricyclic. Examples of such rings include phenyl,naphthalenyl, anthracenyl, indenyl or phenanthrenyl. A preferred arylgroup is phenyl. In addition, the terms “heteroaryl”, “heteroaromaticring” or “heteroaromatic ring system” refer to an aromatic ring systemcontaining at least one heteroatom and consisting either of a singlering or of two or more fused rings. Preferably, single rings willcontain up to three and bicyclic systems up to four heteroatoms whichwill preferably be chosen from nitrogen, oxygen and sulphur. Examples ofsuch groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, 1,2,3-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl,1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl,1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, 1,2,3-triazinyl, 1,2,4-triazinyl,1,3,5-triazinyl, benzofuryl, benzisofuryl, benzothienyl, benzisothienyl,indolyl, isoindolyl, indazolyl, benzothiazolyl, benzisothiazolyl,benzoxazolyl, benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole,quinolinyl, isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl,quinoxalinyl, naphthyridinyl, benzotriazinyl, purinyl, pteridinyl andindolizinyl. Preferred examples of heteroaromatic radicals includepyridyl, pyrimidyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl,2,1,3-benzoxadiazole and thiazolyl.

The terms heterocycle and heterocyclyl refer to a non-aromaticmonocyclic or bicyclic ring system containing up to 10 atoms includingone or more (preferably one or two) heteroatoms selected from O, S andN. Examples of such rings include 1,3-dioxolane, oxetane,tetrahydrofuran, morpholine, thiomorpholine and piperazine.

When present, the optional substituents on heterocyclyl include C₁₋₆alkyl and C₁₋₆ haloalkyl as well as those optional substituents givenabove for an alkyl moiety.

Cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Cycloalkenyl includes cyclopentenyl and cyclohexenyl.

When present, the optional substituents on cycloalkyl or cycloalkenylinclude C₁₋₃ alkyl as well as those optional substituents given abovefor an alkyl moiety.

Carbocyclic rings include aryl, cycloalkyl and cycloalkenyl groups.

When present, the optional substituents on aryl or heteroaryl areselected independently, from halogen, nitro, cyano, rhodano,isothiocyanato, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy-(C₁₋₆)alkyl,C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃₋₇ cycloalkyl (itselfoptionally substituted with C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl(itself optionally substituted with C₁₋₆ alkyl or halogen), hydroxy,C₁₋₁₀ alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy,tri(C₁₋₄)alkyl-silyl(C₁₋₆)alkoxy, C₁₋₆ alkoxycarbonyl(C₁₋₁₀)alkoxy,C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)alkoxy (where the aryl group is optionallysubstituted with halogen or C₁₋₆ alkyl), C₃₋₇ cycloalkyloxy (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),C₂₋₁₀ alkenyloxy, C₂₋₁₀ alkynyloxy, SH, C₁₋₁₀ alkylthio, C₁₋₁₀haloalkylthio, aryl(C₁₋₄)alkylthio C₃₋₇ cycloalkylthio (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),tri(C₁₋₄)-alkylsilyl(C₁₋₆)alkylthio, arylthio, C₁₋₆ alkylsulfonyl, C₁₋₆haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl,arylsulfonyl, tri(C₁₋₄)alkylsilyl, aryldi(C₁₋₄)-alkylsilyl,(C₁₋₄)alkyldiarylsilyl, triarylsilyl, C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆alkyl)-aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆alkylcarbonyloxy, arylcarbonyloxy, di(C₁₋₆)alkylamino-carbonyloxy, aryl(itself optionally substituted with C₁₋₆ alkyl or halogen), heteroaryl(itself optionally substituted with C₁₋₆ alkyl or halogen), heterocyclyl(itself optionally substituted with C₁₋₆ alkyl or halogen), aryloxy(where the aryl group is optionally substituted with C₁₋₆ alkyl orhalogen), heteroaryloxy (where the heteroaryl group is optionallysubstituted with C₁₋₆ alkyl or halogen), heterocyclyloxy (where theheterocyclyl group is optionally substituted with C₁₋₆ alkyl orhalogen), amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆alkylcarbonylamino, N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino,arylcarbonyl, (where the aryl group is itself optionally substitutedwith halogen or C₁₋₆ alkyl) or two adjacent positions on an aryl orheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen or C₁₋₆ alkyl. Further substituents for aryl or heteroarylinclude aryl carbonyl amino (where the aryl group is substituted by C₁₋₆alkyl or halogen), (C₁₋₆)alkyloxycarbonylamino(C₁₋₆)alkyloxycarbonyl-N—(C₁₋₆)alkylamino, aryloxycarbonylamino (wherethe aryl group is substituted by C₁₋₆ alkyl or halogen),aryloxycarbonyl-N—(C₁₋₆)alkylamino, (where the aryl group is substitutedby C₁₋₆ alkyl or halogen), arylsulphonylamino (where the aryl group issubstituted by C₁₋₆ alkyl or halogen), arylsulphonyl-N—(C₁₋₆)alkylamino(where the aryl group is substituted by C₁₋₆ alkyl or halogen),aryl-N—(C₁₋₆)alkylamino (where the aryl group is substituted by C₁₋₆alkyl or halogen), arylamino (where the aryl group is substituted byC₁₋₆ alkyl or halogen), heteroaryl amino (where the heteroaryl group issubstituted by C₁₋₆ alkyl or halogen), heterocyclylamino (where theheterocyclyl group is substituted by C₁₋₆ alkyl or halogen),aminocarbonylamino, C₁₋₆ alkylaminocarbonyl amino,di(C₁₋₆)alkylaminocarbonyl amino, arylaminocarbonyl amino where the arylgroup is substituted by C₁₋₆ alkyl or halogen),aryl-N—(C₁₋₆)alkylaminocarbonylamino where the aryl group is substitutedby C₁₋₆ alkyl or halogen), C₁₋₆ alkylaminocarbonyl-N—(C₁₋₆)alkyl amino,di(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkyl amino,arylaminocarbonyl-N—(C₁₋₆)alkyl amino where the aryl group issubstituted by C₁₋₆ alkyl or halogen) andaryl-N—(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkyl amino where the aryl groupis substituted by C₁₋₆ alkyl or halogen).

For substituted phenyl moieties, heterocyclyl and heteroaryl groups itis preferred that one or more substituents are independently selectedfrom halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₁₋₆alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, C₁₋₆alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, C₁₋₆ alkylsulfonyl, C₁₋₆haloalkylsulfonyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃₋₇cycloalkyl, nitro, cyano, CO₂H, C₁₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl,aryl, heteroaryl, R⁵⁰R⁵¹N or R⁵²R⁵³NC(O); wherein R⁵⁰, R⁵¹, R⁵² and R⁵³are, independently, hydrogen or C₁₋₆ alkyl.

Haloalkenyl groups are alkenyl groups which are substituted with one ormore of the same or different halogen atoms.

It is to be understood that dialkylamino substituents include thosewhere the dialkyl groups together with the N atom to which they areattached form a five, six or seven-membered heterocyclic ring which maycontain one or two further heteroatoms selected from O, N or S and whichis optionally substituted by one or two independently selected(C₁₋₆)alkyl groups. When heterocyclic rings are formed by joining twogroups on an N atom, the resulting rings are suitably pyrrolidine,piperidine, thiomorpholine and morpholine each of which may besubstituted by one or two independently selected (C₁₋₆) alkyl groups.

Preferably the optional substituents on an alkyl moiety include one ormore of halogen, nitro, cyano, HO₂C, C₁₋₁₀ alkoxy (itself optionallysubstituted by C₁₋₁₀ alkoxy), aryl(C₁₋₄)alkoxy, C₁₋₁₀ alkylthio, C₁₋₁₀alkylcarbonyl, C₃₋₅ cycloalkylcarbonyl, C₁₋₁₀ alkoxycarbonyl, C₁₋₆alkylaminocarbonyl, di(C₁₋₆ alkyl)aminocarbonyl, (C₁₋₆)alkylcarbonyloxy,optionally substituted phenyl, heteroaryl, aryloxy, arylcarbonyloxy,heteroaryloxy, heterocyclyl, heterocyclyloxy, C₃₋₇ cycloalkyl (itselfoptionally substituted with (C₁₋₆)alkyl or halogen), C₃₋₇ cycloalkyloxy,C₅₋₇ cycloalkenyl, C₁₋₆ alkylsulfonyl, C₁₋₆ alkylsulfinyl,tri(C₁₋₄)alkylsilyl, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy,aryldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl and triarylsilyl.

Preferably the optional substituents on alkenyl or alkynyl include oneor more of halogen, aryl and C₃₋₇ cycloalkyl.

A preferred optional substituent for heterocyclyl is C₁₋₃ alkyl.

Preferably the optional substituents for cycloalkyl include halogen,cyano and C₁₋₆ alkyl.

The optional substituents for cycloalkenyl preferably include C₁₋₃alkyl, halogen and cyano.

Preferred groups for T, Y, R¹, R², R⁴, R⁹, and R¹⁰ in any combinationthereof are set out below.

Y is preferably O, S, S(O), SO₂, NR³ or CR⁵R⁶ where R³, R⁵ and R⁶ aredefined above. R³ is especially hydrogen, formyl, C₁₋₆ alkylcarbonyl,cyclopropylcarbonyl, C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylsulfonyl, C₁₋₆alkyl, C₁₋₆ haloalkyl, C₃₋₄ alkenyl, C₃₋₄ haloalkenyl, C₃₋₄ alkynyl orbenzyl, or phenyl (where the phenyl containing groups are optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN or NO₂). Especially R⁵ and R⁶ are independently hydrogen,hydroxy, halogen, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, phenyl(C₁₋₃)alkyl (wherein the phenyl group may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), C₃₋₅ cycloalkyl, 1,3-dioxolan-2-yl, phenyl (which may beoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl, or two adjacentpositions on the phenyl ring may be cyclised to form a 5, 6 or 7membered carbocyclic or heterocyclic ring, itself optionally substitutedwith halogen), C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkenyloxy, C₁₋₆alkynyloxy, C₁₋₃ alkoxy(C₁₋₃)alkoxy, benzyloxy (where phenyl isoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂), C₁₋₆ alkylthio, C₁₋₆haloalkylthio, NR⁵⁴R⁵⁵ (where R⁵⁴ and R⁵⁵ are independently hydrogen,C₁₋₆ alkyl or C₁₋₆ haloalkyl, C₁₋₄ alkoxy(C₁₋₄alkyl, formyl, C₂₋₆alkylcarbonyl, phenylcarbonyl (where the phenyl is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂)), or R⁵ and R⁶ together with the carbon atom towhich they are attached form a three to six membered ring, thatoptionally may contain one or two sulfur or one or two not adjacentoxygen atoms or a group NR⁵⁶ (where R⁵⁶ is hydrogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₄ alkoxy(C₁₋₄alkyl, formyl, C₂₋₆ alkylcarbonyl), or whenR⁵ together with R¹ forms a bond, or either R⁵ or R⁶ together with R¹ orR² and the carbon atom they are attached form a three to six memberedring, that optionally may contain one or two not adjacent oxygen atoms,or when R⁵ and R⁶ together form ═O, ═S, ═NR⁵⁷ or ═CR⁵⁸R⁵⁹, wherein R⁵⁷is OH, optionally substituted C₁₋₆ alkoxy or C₁₋₄ alkylcarbonylamino,and R⁵⁸ and R⁵⁹ are independently H or C₁₋₆ alkyl.

More preferably Y is O or CR⁵R⁶ where R⁵ and R⁶ are hydrogen, hydroxy,fluoro, chloro, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆haloalkoxy, C₁₋₆ alkenyloxy, C₁₋₆ alkynyloxy, C₁₋₃ alkoxy(C₁₋₃)alkoxy orbenzyloxy, or R⁵ and R⁶ together with the carbon atom to which they areattached form a three to six membered carbocyclic ring, or R⁵ and R¹together form a bond, or R⁵ together with R¹ and the carbon atoms towhich they are attached form a three to six membered carbocyclic ring.

Most preferably Y is CR⁵R⁶ where R⁵ and R⁶ are independently hydrogen ormethyl, especially hydrogen.

Preferably each R¹ and R² group is independently hydrogen, hydroxy,halogen, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl,phenyl(C₁₋₃)alkyl (wherein the phenyl group may be optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂, aryl, heteroaryl, amino, dialkylamino, C₁₋₆alkylsulfonyl, C₁₋₆ alkoxycarbonyl), C₃₋₅ cycloalkyl, 1,3-dioxolan-2-yl,phenyl (which may be optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl,amino, dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl), C₁₋₆alkoxy, C₁₋₆ haloalkoxy, C₂₋₆ alkenyloxy, C₂₋₆ alkinyloxy, C₁₋₃alkoxy(C₁₋₃)alkoxy, benzyloxy (wherein the phenyl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂), C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, formyl, C₂₋₆alkylcarbonyl, phenylcarbonyl (where the phenyl is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂), or R¹ and R² together are ═O, ═S, ═NR⁶⁰ or═CR⁶¹R⁶², wherein R⁶⁰ is OH, C₁-C₆-alkoxy or C₁-C₆-alkylcarbonylamino,and R⁶¹ and R⁶² are independently H, C₁-C₆-alkyl, or C₁-C₆-haloalkyl; orR¹ and R⁹ together with the carbon atom they are attached form a threeto six membered ring, that optionally may contain one or two notadjacent oxygen atoms; or R¹ and R² together form a three to sixmembered ring, that optionally may contain one or two non-adjacentoxygen atoms.

More preferably each R¹ and R² group is independently hydrogen, hydroxy,halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆alkenyloxy, C₁₋₆ alkynyloxy, C₁₋₃ alkoxy(C₁₋₃)alkoxy or benzyloxy.

Most preferably each R¹ and R² group is independently hydrogen ormethyl.

R⁹ is preferably hydrogen, C₁₋₆ alkyl, C₁₋₆ cyanoalkyl, C₁₋₆ haloalkyl,C₃₋₇ cycloalkyl(C₁₋₄alkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, aryl(C₁₋₆)alkyl(wherein the aryl group may be optionally substituted by halo, nitro,cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆alkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylthio, C₁₋₆ alkoxycarbonyl,C₁₋₆ alkylcarbonylamino, arylcarbonyl), C₂₋₆ alkylcarbonyl,phenylcarbonyl (where the phenyl is optionally substituted by halogen,C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl,heteroaryl, amino or dialkylamino), C₁₋₆ alkoxycarbonyl, C(O)NR⁶³R⁶⁴(where R⁶³ and R⁶⁴ are independently hydrogen, C₁₋₆ alkyl or C₁₋₆haloalkyl or C₁₋₆ alkoxy(C₁₋₆)alkyl or R⁶³ and R⁶⁴ together with the Natom to which they are attached form a five, six or seven-membered ringcontaining an O or S atom), or R⁹ and R¹ together with the carbon atomsto which they are attached form a three to six membered ring.

More preferably R⁹ is independently hydrogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₃₋₇ cycloalkyl(C₁₋₄)alkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl,aryl(C₁₋₆)alkyl (wherein the aryl group may be optionally substituted byhalo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy), C₂₋₆alkylcarbonyl, phenylcarbonyl (where the phenyl is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl), C₁₋₆alkoxycarbonyl, or R⁹ and R¹ together with the carbon atoms to whichthey are attached form a three to six membered ring.

Most preferably R₉ is independently hydrogen or methyl.

Preferably each R⁴ is independently halogen, cyano, C₁₋₈ alkyl, C₁₋₈haloalkyl, cyano(C₁₋₆)alkyl, C₁₋₃ alkoxy(C₁₋₃)alkyl, C₂₋₆ alkynyl, C₃₋₆cycloalkyl, C₁₋₃ alkyl (C₃₋₆) cycloalkyl, phenyl (optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂, aryl, heteroaryl, amino or dialkylamino), heterocyclyl(optionally substituted by halo, nitro, cyano, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy or C₁₋₆ haloalkoxy), formyl, C₁₋₆ alkylcarbonyl,C₁₋₆ alkoxycarbonyl, C₁₋₆ alkylthiocarbonyl, C₁₋₆ alkoxythiocarbonyl,carbamoyl, C₁₋₆ alkylaminocarbonyl, di-C₁₋₆ alkylaminocarbonyl,thiocarbamoyl, C₁₋₆ alkylaminothiocarbonyl, di-C₁₋₆alkylaminothiocarbonyl, C₁₋₈ alkoxy, C₁₋₆ haloalkoxy, phenoxy(optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, phenyl), heteroaryloxy (optionallysubstituted by halo, nitro, cyano, C₁₋₃ alkyl, C₁₋₃ haloalkyl, C₁₋₃alkoxy or C₁₋₃ haloalkoxy), C₁₋₆ alkylcarbonyloxy, C₁₋₆alkoxycarbonyloxy, C₁₋₆ alkylaminocarbonyloxy, di-C₁₋₆alkylaminocarbonyloxy, C₁₋₆ alkylaminothiocarbonyloxy, di-C₁₋₆alkylaminothiocarbonyloxy, C₁₋₈ alkylthio, C₁₋₆ haloalkylthio, arylthioor heteroarylthio (where the aryl is optionally substituted by halogen,C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂ orphenyl), C₁₋₆ alkylcarbonylthio, C₁₋₆ alkylaminocarbonylthio, di-C₁₋₆alkylaminocarbonylthio, di(C₁₋₈)alkylamino, C₁₋₆ alkylcarbonylamino,C₁₋₆ alkoxycarbonylamino, C₁₋₆ alkylaminocarbonylamino, di-C₁₋₆alkylaminocarbonylamino, aminothiocarbonylamino, C₁₋₆alkylaminothiocarbonylamino, di-C₁₋₆ alkylaminothiocarbonylamino, or 2adjacent groups R⁴ together with the carbon atoms to which they areattached form a 4, 5, 6 or 7 membered carbocyclic or heterocyclic ringwhich may be optionally substituted by halogen; n is 0, 1, 2 or 3.

More preferably each R⁴ is independently halogen, cyano, C₁₋₈ alkyl,C₁₋₈ haloalkyl, cyano(C₁₋₆)alkyl, C₁₋₆ alkoxy(C₁₋₆)alkyl, C₂₋₆ alkynyl,heterocyclyl (optionally substituted by C₁₋₆ alkyl), C₁₋₈ alkoxy, C₁₋₆haloalkoxy, phenoxy (optionally substituted by halo, cyano, C₁₋₃ alkylor C₁₋₃ haloalkyl), heteroaryloxy (optionally substituted by halo,cyano, C₁₋₃ alkyl or C₁₋₃ haloalkyl), C₁₋₃ alkoxy, C₁₋₃ haloalkoxy, C₁₋₃alkylthio, C₁₋₃ haloalkylthio, C₁₋₃ alksulfonyl, di(C₁₋₈)alkylamino, or2 adjacent groups R⁴ together with the carbon atoms to which they areattached form a 4, 5, 6 or 7 membered carbocyclic or heterocyclic ringwhich may be optionally substituted by halogen; n is 0, 1, 2 or 3.

Most preferably each R⁴ is independently fluoro, chloro, bromo, C₁₋₄alkyl or C₁₋₄ haloalkyl; n is 1, 2 or 3, preferably 1 or 2.

Preferably at least one group R⁴ is positioned adjacent to the group Y.

R¹⁰ is preferably hydrogen, hydroxy, cyano, C₁₋₆ alkyl, C₁₋₆ haloalkyl,C₁₋₆ alkoxy(C₁₋₆)alkyl, phenyl(C₁₋₃)alkyl (wherein the phenyl group maybe optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂, aryl, heteroaryl, amino,dialkylamino, C₁₋₆ alkylsulfonyl, C₁₋₆ alkoxycarbonyl), C₁₋₆ alkoxy,C₁₋₆ haloalkoxy, C₂₋₆ alkenyloxy, C₂₋₆ alkinyloxy, C₁₋₃alkoxy(C₁₋₃)alkoxy, benzyloxy (wherein the phenyl group is optionallysubstituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄haloalkoxy, CN, NO₂), C₁₋₆ alkylthio, C₁₋₆ haloalkylthio, phenylthio(where the phenyl is optionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂), C₁₋₆ alkyldithio,C₁₋₆ haloalkyldithio, formyl, C₂₋₆ alkylcarbonyl, C₂₋₆haloalkylcarbonyl, C₁₋₆ alkoxycarbonyl, arylcarbonyl (where the aryl isoptionally substituted by halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄haloalkyl, C₁₋₄ haloalkoxy, CN, NO₂), NR⁶⁵R⁶⁶ (where R⁶⁵ and R⁶⁶ areindependently hydrogen, C₁₋₆ alkyl or C₁₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, C₁₋₆ alkylcarbonyl or R⁶⁵ and R⁶⁶ together with the Natom to which they are attached form a five, six or seven-membered ringcontaining an O or S atom), R⁶⁵R⁶⁶NS, R⁶⁵R⁶⁶NC(O), R⁶⁵R⁶⁶NC(S),R⁶⁷N═C(R⁶⁸)—, where R⁶⁷ is C₁₋₆ alkyl or phenyl (optionally substitutedby halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄ haloalkyl, C₁₋₄ haloalkoxy,CN, NO₂), and R⁶⁸ is H, C₁₋₆ alkyl or C₁₋₆ alkylthio.

More preferably R¹⁰ is hydrogen, hydroxy, cyano, C₁₋₆ alkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, C₁₋₆ alkoxy, C₁₋₆ alkylthio, C₁₋₆ haloalkylthio,formyl, C₂₋₆ alkylcarbonyl, C₁₋₆ alkoxycarbonyl, NR⁶⁵R⁶⁶ (where R⁶⁵ andR⁶⁶ are independently hydrogen, C₁₋₆ alkyl or C₁₋₆ haloalkyl, C₁₋₆alkoxy(C₁₋₆)alkyl, C₁₋₆ alkylcarbonyl or R⁶⁵ and R⁶⁶ together with the Natom to which they are attached form a five, six or seven-membered ringcontaining an O or S atom).

Most preferably R¹⁰ is hydrogen, cyano, or formyl, especially hydrogen.

It is preferred that the ring

is a 6-membered aromatic ring or is 5 or 6 membered heteroaromatic ringwherein the ring members are each independently CH, S, N, NR⁴, O, or CR⁴provided that there are no more than one O or S atoms present in thering.

More preferably the ring

is a benzene, thiophene, furan, pyridine, pyrimidine, pyrazine,pyridazine, triazine, pyrrole, imidazole, pyrazole, oxazole, thiazole,isoxazole, isothiazole, [1,2,3]triazole, [1,2,3]oxadiazole or[1,2,3]thiadiazole

Most preferably the ring

is a benzene, pyridine or thiophene ring, especially a benzene ring.

Another especially preferred group of compounds are those compounds offormula (IB

where the chirality on the R⁹ bearing carbon atom is that shown in theabove structure and R¹, R², R⁴, R⁹, R¹⁰, Y and n are as defined above inrelation to formula (I).

Certain compounds of formula (I) are novel and as such form a furtheraspect of the invention. One group of novel compounds are compounds offormula IC

wherein R¹, R², R⁴, R⁹, T, X, Y and n are as defined in in claim 1 orsalts or N-oxides thereof, with the proviso that the following compounds(IC1) to (IC3) are excluded:

wherein R¹⁰⁰ is hydrogen or acetyl, and

wherein R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ are hydrogen, R²⁰⁰ and R³⁰⁰ areindependently of each other halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄alkylthio, trifluoromethyl or trifluoromethoxy, where s and t areindependently of each other 0, 1, 2 or 3, and the total of s+t is notgreater than 3.

A preferred group of new compounds of the formula IC are those of theformula ID

or salts or N-oxides thereof, wherein Y is CR⁵R⁶ or CR⁵R⁶CR⁷R⁸, and R¹,R², R⁴, R⁹, X and n are as defined above, where at least one of R¹, R²,R⁴, R⁵, R⁶, R⁷, R⁸ or R⁹ is fluorine, and those of formula IE

or salts or N-oxides thereof, wherein Y is CR⁵R⁶, and R¹, R², R⁴, R⁹, Xare as defined above and n is 0, 1, 2 or 3.

The compounds in Tables I to LXIII below illustrate the compounds of theinvention.

Table I provides 612 compounds of formula Ia

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

TABLE 1 Compound No R9 R1 R2 R7 R8 R4a R4b R4c R4d I-1 Me H H H H H H HH I-2 Et H H H H H H H H I-3 Vinyl H H H H H H H H I-4 Allyl H H H H H HH H I-5 cyclopropyl H H H H H H H H I-6 CN H H H H H H H H I-7 CONH₂ H HH H H H H H I-8 CONHMe H H H H H H H H I-9 CONMe₂ H H H H H H H H I-10COMe H H H H H H H H I-11 COOH H H H H H H H H I-12 COOMe H H H H H H HH I-13 CSNHMe H H H H H H H H I-14 H Me H H H H H H H I-15 H Et H H H HH H H I-16 H vinyl H H H H H H H I-17 H allyl H H H H H H H I-18 Hcyclopropyl H H H H H H H I-19 H F H H H H H H H I-20 H Cl H H H H H H HI-21 H NO₂ H H H H H H H I-22 H CN H H H H H H H I-23 H CONH₂ H H H H HH H I-24 H CONHMe H H H H H H H I-25 H CONMe₂ H H H H H H H I-26 H COMeH H H H H H H I-27 H COOH H H H H H H H I-28 H COOMe H H H H H H H I-29H CSOMe H H H H H H H I-30 H CSNH₂ H H H H H H H I-31 H CSNMe₂ H H H H HH H I-32 H CSNHMe H H H H H H H I-33 H OMe H H H H H H H I-34 H OEt H HH H H H H I-35 H OCOMe H H H H H H H I-36 H OCOOMe H H H H H H H I-37 HOCONHMe H H H H H H H I-38 H OCONMe₂ H H H H H H H I-39 H OCSMe H H H HH H H I-40 H OCSNMe₂ H H H H H H H I-41 H SMe H H H H H H H I-42 H SEt HH H H H H H I-43 H SCOMe H H H H H H H I-44 H SCSNMe₂ H H H H H H H I-45H SCSNHMe H H H H H H H I-46 H NHMe H H H H H H H I-47 H NH₂ H H H H H HH I-48 H NMe₂ H H H H H H H I-49 H NHCOMe H H H H H H H I-50 H NHCONH₂ HH H H H H H I-51 H NHCONHMe H H H H H H H I-52 H NHCONMe₂ H H H H H H HI-53 H phenyl H H H H H H H I-54 H 2-chloro- H H H H H H H phenyl I-55 H4-nitrophenyl H H H H H H H I-56 H 2-pyridyl H H H H H H H I-57 H3-pyridyl H H H H H H H I-58 H 4-pyridyl H H H H H H H I-59 H 2-furyl HH H H H H H I-60 H PhO H H H H H H H I-61 CH₂ H H H H H H H I-62 H ═O HH H H H H I-63 H ═NOH H H H H H H I-64 H ═NOMe H H H H H H I-65 H ═CH₂ HH H H H H I-66 H ═CHMe H H H H H H I-67 H H H H H H H H H I-68 H H H MeH H H H H I-69 H H H Et H H H H H I-70 H H H Vinyl H H H H H I-71 H H HAllyl H H H H H I-72 H H H cyclopropyl H H H H H I-73 H H H F H H H H HI-74 H H H Cl H H H H H I-75 H H H NO₂ H H H H H I-76 H H H CN H H H H HI-77 H H H CONH₂ H H H H H I-78 H H H CONHMe H H H H H I-79 H H H CONMe₂H H H H H I-80 H H H COMe H H H H H I-81 H H H COOH H H H H H I-82 H H HCOOMe H H H H H I-83 H H H CSOMe H H H H H I-84 H H H CSNH₂ H H H H HI-85 H H H CSNMe₂ H H H H H I-86 H H H CSNHMe H H H H H I-87 H H H OMe HH H H H I-88 H H H OEt H H H H H I-89 H H H OCOMe H H H H H I-90 H H HOCOOMe H H H H H I-91 H H H OCONHMe H H H H H I-92 H H H OCONMe₂ H H H HH I-93 H H H OCSMe H H H H H I-94 H H H OCSNMe₂ H H H H H I-95 H H H SMeH H H H H I-96 H H H SEt H H H H H I-97 H H H SCOMe H H H H H I-98 H H HSCSNMe₂ H H H H H I-99 H H H SCSNHMe H H H H H I-100 H H H NHMe H H H HH I-101 H H H NH₂ H H H H H I-102 H H H NMe₂ H H H H H I-103 H H HNHCOMe H H H H H I-104 H H H NHCONH₂ H H H H H I-105 H H H NHCONHMe H HH H H I-106 H H H NHCONMe₂ H H H H H I-107 H H H Phenyl H H H H H I-108H H H 2-chloro- H H H H H phenyl I-109 H H H 4- H H H H H nitrophenylI-110 H H H 2-pyridyl H H H H H I-111 H H H 3-pyridyl H H H H H I-112 HH H 4-pyridyl H H H H H I-113 H H H 2-furyl H H H H H I-114 H H H PhO HH H H H I-115 H H H ═O H H H H I-116 H H H ═NOH H H H H I-117 H H H═NOMe H H H H I-118 H H H ═CH₂ H H H H I-119 H H H ═CHMe H H H H I-120 HMe H Me H H H H H I-121 H Me F Me H H H H H I-122 H Me H F H H H H HI-123 H Me F H H H H H H I-124 H Me Me H H H H H H I-125 H F H Me H H HH H I-126 H F H F H H H H H I-127 Me H H H H F H H H I-128 Et H H H H FH H H I-129 vinyl H H H H F H H H I-130 allyl H H H H F H H H I-131cyclopropyl H H H H F H H H I-132 CN H H H H F H H H I-133 CONH₂ H H H HF H H H I-134 CONHMe H H H H F H H H I-135 CONMe₂ H H H H F H H H I-136COMe H H H H F H H H I-137 COOH H H H H F H H H I-138 COOMe H H H H F HH H I-139 CSNHMe H H H H F H H H I-140 H Me H H H F H H H I-141 H Et H HH F H H H I-142 H vinyl H H H F H H H I-143 H allyl H H H F H H H I-144H cyclopropyl H H H F H H H I-145 H F H H H F H H H I-146 H Cl H H H F HH H I-147 H NO₂ H H H F H H H I-148 H CN H H H F H H H I-149 H CONH₂ H HH F H H H I-150 H CONHMe H H H F H H H I-151 H CONMe₂ H H H F H H HI-152 H COMe H H H F H H H I-153 H COOH H H H F H H H I-154 H COOMe H HH F H H H I-155 H CSOMe H H H F H H H I-156 H CSNH₂ H H H F H H H I-157H CSNMe₂ H H H F H H H I-158 H CSNHMe H H H F H H H I-159 H OMe H H H FH H H I-160 H OEt H H H F H H H I-161 H OCOMe H H H F H H H I-162 HOCOOMe H H H F H H H I-163 H OCONHMe H H H F H H H I-164 H OCONMe₂ H H HF H H H I-165 H OCSMe H H H F H H H I-166 H OCSNMe₂ H H H F H H H I-167H SMe H H H F H H H I-168 H SEt H H H F H H H I-169 H SCOMe H H H F H HH I-170 H SCSNMe₂ H H H F H H H I-171 H SCSNHMe H H H F H H H I-172 HNHMe H H H F H H H I-173 H NH₂ H H H F H H H I-174 H NMe₂ H H H F H H HI-175 H NHCOMe H H H F H H H I-176 H NHCONH₂ H H H F H H H I-177 HNHCONHMe H H H F H H H I-178 H NHCONMe₂ H H H F H H H I-179 H phenyl H HH F H H H I-180 H 2-chloro- H H H F H H H phenyl I-181 H 4-nitrophenyl HH H F H H H I-182 H 2-pyridyl H H H F H H H I-183 H 3-pyridyl H H H F HH H I-184 H 4-pyridyl H H H F H H H I-185 H 2-furyl H H H F H H H I-186H PhO H H H F H H H I-187 CH₂ H H H F H H H I-188 H H H Me H F H H HI-190 H H H Vinyl H F H H H I-191 H H H Allyl H F H H H I-192 H H HCyclopropyl H F H H H I-193 H H H F H F H H H I-194 H H H Cl H F H H HI-195 H H H NO₂ H F H H H I-196 H H H CN H F H H H I-197 H H H CONH₂ H FH H H I-198 H H H CONHMe H F H H H I-199 H H H CONMe₂ H F H H H I-200 HH H COMe H F H H H I-201 H H H COOH H F H H H I-202 H H H COOMe H F H HH I-203 H H H CSOMe H F H H H I-204 H H H CSNH₂ H F H H H I-205 H H HCSNMe₂ H F H H H I-206 H H H CSNHMe H F H H H I-207 H H H OMe H F H H HI-208 H H H OEt H F H H H I-209 H H H OCOMe H F H H H I-210 H H H OCOOMeH F H H H I-211 H H H OCONHMe H F H H H I-212 H H H OCONMe₂ H F H H HI-213 H H H OCSMe H F H H H I-214 H H H OCSNMe2 H F H H H I-215 H H HSMe H F H H H I-216 H H H SEt H F H H H I-217 H H H SCOMe H F H H HI-218 H H H SCSNMe₂ H F H H H I-219 H H H SCSNHMe H F H H H I-220 H H HNHMe H F H H H I-221 H H H NH₂ H F H H H I-222 H H H NMe₂ H F H H HI-223 H H H NHCOMe H F H H H I-224 H H H NHCONH₂ H F H H H I-225 H H HNHCONHMe H F H H H I-226 H H H NHCONMe₂ H F H H H I-227 H H H Phenyl H FH H H I-228 H H H 2-chloro- H F H H H phenyl I-229 H H H 4-nitrophenyl HF H H H I-230 H H H 2-pyridyl H F H H H I-231 H H H 3-pyridyl H F H H HI-232 H H H 4-pyridyl H F H H H I-233 H H H 2-furyl H F H H H I-234 H HH PhO H F H H H I-235 H Me H Me H F H H H I-236 H Me F Me H F H H HI-237 H Me H F H F H H H I-238 H Me F H H F H H H I-239 H Me Me H H F HH H I-240 H F H Me H F H H H I-241 H F H F H F H H H I-242 Me H H H H MeH H H I-243 Et H H H H Me H H H I-244 vinyl H H H H Me H H H I-245 allylH H H H Me H H H I-246 cyclopropyl H H H H Me H H H I-247 CN H H H H MeH H H I-248 CONH₂ H H H H Me H H H I-249 CONHMe H H H H Me H H H I-250CONMe₂ H H H H Me H H H I-251 COMe H H H H Me H H H I-252 COOH H H H HMe H H H I-253 COOMe H H H H Me H H H I-254 CSNHMe H H H H Me H H HI-255 H Me H H H Me H H H I-256 H Et H H H Me H H H I-257 H vinyl H H HMe H H H I-258 H allyl H H H Me H H H I-259 H cyclopropyl H H H Me H H HI-260 H F H H H Me H H H I-261 H Cl H H H Me H H H I-262 H NO₂ H H H MeH H H I-263 H CN H H H Me H H H I-264 H CONH₂ H H H Me H H H I-265 HCONHMe H H H Me H H H I-266 H CONMe₂ H H H Me H H H I-267 H COMe H H HMe H H H I-268 H COOH H H H Me H H H I-269 H COOMe H H H Me H H H I-270H CSOMe H H H Me H H H I-271 H CSNH₂ H H H Me H H H I-272 H CSNMe₂ H H HMe H H H I-273 H CSNHMe H H H Me H H H I-274 H OMe H H H Me H H H I-275H OEt H H H Me H H H I-276 H OCOMe H H H Me H H H I-277 H OCOOMe H H HMe H H H I-278 H OCONHMe H H H Me H H H I-279 H OCONMe₂ H H H Me H H HI-280 H OCSMe H H H Me H H H I-281 H OCSNMe₂ H H H Me H H H I-282 H SMeH H H Me H H H I-283 H SEt H H H Me H H H I-284 H SCOMe H H H Me H H HI-285 H SCSNMe₂ H H H Me H H H I-286 H SCSNHMe H H H Me H H H I-287 HNHMe H H H Me H H H I-288 H NH₂ H H H Me H H H I-289 H NMe₂ H H H Me H HH I-290 H NHCOMe H H H Me H H H I-291 H NHCONH₂ H H H Me H H H I-292 HNHCONHMe H H H Me H H H I-293 H NHCONMe₂ H H H Me H H H I-294 H phenyl HH H Me H H H I-295 H 2-chloro- H H H Me H H H phenyl I-296 H4-nitrophenyl H H H Me H H H I-297 H 2-pyridyl H H H Me H H H I-298 H3-pyridyl H H H Me H H H I-299 H 4-pyridyl H H H Me H H H I-300 H2-furyl H H H Me H H H I-301 H PhO H H H Me H H H I-302 CH₂ H H H Me H HH I-303 H H H Me H Me H H H I-304 H H H Et H Me H H H I-305 H H H VinylH Me H H H I-306 H H H Allyl H Me H H H I-307 H H H Cyclopropyl H Me H HH I-308 H H H F H Me H H H I-309 H H H Cl H Me H H H I-310 H H H NO₂ HMe H H H I-311 H H H CN H Me H H H I-312 H H H CONH₂ H Me H H H I-313 HH H CONHMe H Me H H H I-314 H H H CONMe₂ H Me H H H I-315 H H H COMe HMe H H H I-316 H H H COOH H Me H H H I-317 H H H COOMe H Me H H H I-318H H H CSOMe H Me H H H I-319 H H H CSNH₂ H Me H H H I-320 H H H CSNMe₂ HMe H H H I-321 H H H CSNHMe H Me H H H I-322 H H H OMe H Me H H H I-323H H H OEt H Me H H H I-324 H H H OCOMe H Me H H H I-325 H H H OCOOMe HMe H H H I-326 H H H OCONHMe H Me H H H I-327 H H H OCONMe₂ H Me H H HI-328 H H H OCSMe H Me H H H I-329 H H H OCSNMe2 H Me H H H I-330 H H HSMe H Me H H H I-331 H H H SEt H Me H H H I-332 H H H SCOMe H Me H H HI-333 H H H SCSNMe₂ H Me H H H I-334 H H H SCSNHMe H Me H H H I-335 H HH NHMe H Me H H H I-336 H H H NH₂ H Me H H H I-337 H H H NMe₂ H Me H H HI-338 H H H NHCOMe H Me H H H I-339 H H H NHCONH₂ H Me H H H I-340 H H HNHCONHMe H Me H H H I-341 H H H NHCONMe₂ H Me H H H I-342 H H H Phenyl HMe H H H I-343 H H H 2-chloro- H Me H H H phenyl I-344 H H H4-nitrophenyl H Me H H H I-345 H H H 2-pyridyl H Me H H H I-346 H H H3-pyridyl H Me H H H I-347 H H H 4-pyridyl H Me H H H I-348 H H H2-furyl H Me H H H I-349 H H H PhO H Me H H H I-350 H Me H Me H Me H H HI-351 H Me F Me H Me H H H I-352 H Me H F H Me H H H I-353 H Me F H H MeH H H I-354 H Me Me H H Me H H H I-355 H F H Me H Me H H H I-356 H F H FH Me H H H I-357 Me H H H H F H F H I-358 Et H H H H F H F H I-359 vinylH H H H F H F H I-360 allyl H H H H F H F H I-361 cyclopropyl H H H H FH F H I-362 CN H H H H F H F H I-363 CONH₂ H H H H F H F H I-364 CONHMeH H H H F H F H I-365 CONMe₂ H H H H F H F H I-366 COMe H H H H F H F HI-367 COOH H H H H F H F H I-368 COOMe H H H H F H F H I-369 CSNHMe H HH H F H F H I-370 H Me H H H F H F H I-371 H Et H H H F H F H I-372 Hvinyl H H H F H F H I-373 H allyl H H H F H F H I-374 H cyclopropyl H HH F H F H I-375 H F H H H F H F H I-376 H Cl H H H F H F H I-377 H NO₂ HH H F H F H I-378 H CN H H H F H F H I-379 H CONH₂ H H H F H F H I-380 HCONHMe H H H F H F H I-381 H CONMe₂ H H H F H F H I-382 H COMe H H H F HF H I-383 H COOH H H H F H F H I-384 H COOMe H H H F H F H I-385 H CSOMeH H H F H F H I-386 H CSNH₂ H H H F H F H I-387 H CSNMe₂ H H H F H F HI-388 H CSNHMe H H H F H F H I-389 H OMe H H H F H F H I-390 H OEt H H HF H F H I-391 H OCOMe H H H F H F H I-392 H OCOOMe H H H F H F H I-393 HOCONHMe H H H F H F H I-394 H OCONMe₂ H H H F H F H I-395 H OCSMe H H HF H F H I-396 H OCSNMe₂ H H H F H F H I-397 H SMe H H H F H F H I-398 HSEt H H H F H F H I-399 H SCOMe H H H F H F H I-400 H SCSNMe₂ H H H F HF H I-401 H SCSNHMe H H H F H F H I-402 H NHMe H H H F H F H I-403 H NH₂H H H F H F H I-404 H NMe₂ H H H F H F H I-405 H NHCOMe H H H F H F HI-406 H NHCONH₂ H H H F H F H I-407 H NHCONHMe H H H F H F H I-408 HNHCONMe₂ H H H F H F H I-409 H phenyl H H H F H F H I-410 H 2-chloro- HH H F H F H phenyl I-411 H 4- H H H F H F H nitrophenyl I-412 H2-pyridyl H H H F H F H I-413 H 3-pyridyl H H H F H F H I-414 H4-pyridyl H H H F H F H I-415 H 2-furyl H H H F H F H I-416 H PhO H H HF H F H I-417 CH₂ H H H F H F H I-418 H H H Me H F H F H I-419 H H H EtH F H F H I-420 H H H Vinyl H F H F H I-421 H H H Allyl H F H F H I-422H H H Cyclopropyl H F H F H I-423 H H H F H F H F H I-424 H H H Cl H F HF H I-425 H H H NO₂ H F H F H I-426 H H H CN H F H F H I-427 H H H CONH₂H F H F H I-428 H H H CONHMe H F H F H I-429 H H H CONMe₂ H F H F HI-430 H H H COMe H F H F H I-431 H H H COOH H F H F H I-432 H H H COOMeH F H F H I-433 H H H CSOMe H F H F H I-434 H H H CSNH₂ H F H F H I-435H H H CSNMe₂ H F H F H I-436 H H H CSNHMe H F H F H I-437 H H H OMe H FH F H I-438 H H H OEt H F H F H I-439 H H H OCOMe H F H F H I-440 H H HOCOOMe H F H F H I-441 H H H OCONHMe H F H F H I-442 H H H OCONMe₂ H F HF H I-443 H H H OCSMe H F H F H I-444 H H H OCSNMe₂ H F H F H I-445 H HH SMe H F H F H I-446 H H H SEt H F H F H I-447 H H H SCOMe H F H F HI-448 H H H SCSNMe₂ H F H F H I-449 H H H SCSNHMe H F H F H I-450 H H HNHMe H F H F H I-451 H H H NH₂ H F H F H I-452 H H H NMe₂ H F H F HI-453 H H H NHCOMe H F H F H I-454 H H H NHCONH₂ H F H F H I-455 H H HNHCONHMe H F H F H I-456 H H H NHCONMe₂ H F H F H I-457 H H H Phenyl H FH F H I-458 H H H 2-chloro- H F H F H phenyl I-459 H H H 4-nitrophenyl HF H F H I-460 H H H 2-pyridyl H F H F H I-461 H H H 3-pyridyl H F H F HI-462 H H H 4-pyridyl H F H F H I-463 H H H 2-furyl H F H F H I-464 H HH PhO H F H F H I-465 H Me H Me H F H F H I-466 H Me F Me H F H F HI-467 H Me H F H F H F H I-468 H Me F H H F H F H I-469 H Me Me H H F HF H I-470 H F H Me H F H F H I-471 H F H F H F H F H I-472 H H H H H MeH H H I-473 H H H H H Et H H H I-474 H H H H H vinyl H H H I-475 H H H HH allyl H H H I-476 H H H H H cyclopropyl H H H I-477 H H H H H F H H HI-478 H H H H H Cl H H H I-479 H H H H H NO₂ H H H I-480 H H H H H CN HH H I-481 H H H H H CONH₂ H H H I-482 H H H H H CONHMe H H H I-483 H H HH H CONMe₂ H H H I-484 H H H H H COMe H H H I-485 H H H H H COOH H H HI-486 H H H H H COOMe H H H I-487 H H H H H CSOMe H H H I-488 H H H H HCSNH₂ H H H I-489 H H H H H CSNMe₂ H H H I-490 H H H H H CSNHMe H H HI-491 H H H H H OMe H H H I-492 H H H H H OEt H H H I-493 H H H H HOCOMe H H H I-494 H H H H H OCOOMe H H H I-495 H H H H H OCONHMe H H HI-496 H H H H H OCONMe₂ H H H I-497 H H H H H OCSMe H H H I-498 H H H HH OCSNMe₂ H H H I-499 H H H H H SMe H H H I-500 H H H H H SEt H H HI-501 H H H H H SCOMe H H H I-502 H H H H H SCSNMe₂ H H H I-503 H H H HH SCSNHMe H H H I-504 H H H H H NHMe H H H I-505 H H H H H NH₂ H H HI-506 H H H H H NMe₂ H H H I-507 H H H H H NHCOMe H H H I-508 H H H H HNHCONH₂ H H H I-509 H H H H H NHCONHMe H H H I-510 H H H H H NHCONMe₂ HH H I-511 H H H H H phenyl H H H I-512 H H H H H 2-chloro- H H H phenylI-513 H H H H H 4- H H H nitrophenyl I-514 H H H H H 2-pyridyl H H HI-515 H H H H H 3-pyridyl H H H I-516 H H H H H 4-pyridyl H H H I-517 HH H H H 2-furyl H H H I-518 H H H H H PhO H H H I-519 H H H H H H H Me HI-520 H H H H H H H Et H I-521 H H H H H H H vinyl H I-522 H H H H H H Hallyl H I-523 H H H H H H H cyclopropyl H I-524 H H H H H H H F H I-525H H H H H H H Cl H I-526 H H H H H H H NO₂ H I-527 H H H H H H H CN HI-528 H H H H H H H CONH₂ H I-529 H H H H H H H CONHMe H I-530 H H H H HH H CONMe₂ H I-531 H H H H H H H COMe H I-532 H H H H H H H COOH H I-533H H H H H H H COOMe H I-534 H H H H H H H CSOMe H I-535 H H H H H H HCSNH₂ H I-536 H H H H H H H CSNMe₂ H I-537 H H H H H H H CSNHMe H I-538H H H H H H H OMe H I-539 H H H H H H H OEt H I-540 H H H H H H H OCOMeH I-541 H H H H H H H OCOOMe H I-542 H H H H H H H OCONHMe H I-543 H H HH H H H OCONMe₂ H I-544 H H H H H H H OCSMe H I-545 H H H H H H HOCSNMe₂ H I-546 H H H H H H H SMe H I-547 H H H H H H H SEt H I-548 H HH H H H H SCOMe H I-549 H H H H H H H SCSNMe₂ H I-550 H H H H H H HSCSNHMe H I-551 H H H H H H H NHMe H I-552 H H H H H H H NH₂ H I-553 H HH H H H H NMe₂ H I-554 H H H H H H H NHCOMe H I-555 H H H H H H HNHCONH₂ H I-556 H H H H H H H NHCONHMe H I-557 H H H H H H H NHCONMe₂ HI-558 H H H H H H H phenyl H I-559 H H H H H H H 2- H chloro- phenylI-560 H H H H H H H 4- H nitrophenyl I-561 H H H H H H H 2- H pyridylI-562 H H H H H H H 3- H pyridyl I-563 H H H H H H H 4- H pyridyl I-564H H H H H H H 2-furyl H I-565 H H H H H H H PhO H I-566 H H H H H H H HMe I-567 H H H H H H H H Et I-568 H H H H H H H H vinyl I-569 H H H H HH H H allyl I-570 H H H H H H H H cyclopropyl I-571 H H H H H H H H FI-572 H H H H H H H H Cl I-573 H H H H H H H H NO₂ I-574 H H H H H H H HCN I-575 H H H H H H H H CONH₂ I-576 H H H H H H H H CONHMe I-577 H H HH H H H H CONMe₂ I-578 H H H H H H H H COMe I-579 H H H H H H H H COOHI-580 H H H H H H H H COOMe I-581 H H H H H H H H CSOMe I-582 H H H H HH H H CSNH₂ I-583 H H H H H H H H CSNMe₂ I-584 H H H H H H H H CSNHMeI-585 H H H H H H H H OMe I-586 H H H H H H H H OEt I-587 H H H H H H HH OCOMe I-588 H H H H H H H H OCOOMe I-589 H H H H H H H H OCONHMe I-590H H H H H H H H OCONMe₂ I-591 H H H H H H H H OCSMe I-592 H H H H H H HH OCSNMe₂ I-593 H H H H H H H H SMe I-594 H H H H H H H H SEt I-595 H HH H H H H H SCOMe I-596 H H H H H H H H SCSNMe₂ I-597 H H H H H H H HSCSNHMe I-598 H H H H H H H H NHMe I-599 H H H H H H H H NH₂ I-600 H H HH H H H H NMe₂ I-601 H H H H H H H H NHCOMe I-602 H H H H H H H HNHCONH₂ I-603 H H H H H H H H NHCONHMe I-604 H H H H H H H H NHCONMe₂I-605 H H H H H H H H phenyl I-606 H H H H H H H H 2-chloro- phenylI-607 H H H H H H H H 4- nitrophenyl I-608 H H H H H H H H 2-pyridylI-609 H H H H H H H H 3-pyridyl I-610 H H H H H H H H 4-pyridyl I-611 HH H H H H H H 2-furyl I-612 H H H H H H H H PhO

Table II provides 612 compounds of formula Ib

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table III provides 612 compounds of formula Ic

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table IV provides 612 compounds of formula Id

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table V provides 612 compounds of formula Ie

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table VI provides 612 compounds of formula If

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table VII provides 612 compounds of formula Ig

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table VIII provides 612 compounds of formula Ih

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table IX provides 612 compounds of formula II

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table X provides 612 compounds of formula Ij

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XI provides 612 compounds of formula Ik

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XII provides 612 compounds of formula II

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R4d, R⁷, R⁸ and R⁹are given in Table 1.

Table XIII provides 612 compounds of formula Im

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XIV provides 612 compounds of formula In

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XV provides 612 compounds of formula Io

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XVI provides 612 compounds of formula Ip

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁷, R⁸ andR⁹ are given in Table 1.

Table XVII provides 612 compounds of formula Iq

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

TABLE 2 Compound No R9 R1 R2 R5 R6 R4a R4b R4c R4d XVII-1 Me H H H H H HH H XVII-2 Et H H H H H H H H XVII-3 vinyl H H H H H H H H XVII-4 allylH H H H H H H H XVII-5 cyclopropyl H H H H H H H H XVII-6 CN H H H H H HH H XVII-7 CONH₂ H H H H H H H H XVII-8 CONHMe H H H H H H H H XVII-9CONMe₂ H H H H H H H H XVII-10 COMe H H H H H H H H XVII-11 COOH H H H HH H H H XVII-12 COOMe H H H H H H H H XVII-13 CSNHMe H H H H H H H HXVII-14 H Me H H H H H H H XVII-15 H Et H H H H H H H XVII-16 H vinyl HH H H H H H XVII-17 H allyl H H H H H H H XVII-18 H cyclopropyl H H H HH H H XVII-19 H F H H H H H H H XVII-20 H Cl H H H H H H H XVII-21 H NO₂H H H H H H H XVII-22 H CN H H H H H H H XVII-23 H CONH₂ H H H H H H HXVII-24 H CONHMe H H H H H H H XVII-25 H CONMe₂ H H H H H H H XVII-26 HCOMe H H H H H H H XVII-27 H COOH H H H H H H H XVII-28 H COOMe H H H HH H H XVII-29 H CSOMe H H H H H H H XVII-30 H CSNH₂ H H H H H H HXVII-31 H CSNMe₂ H H H H H H H XVII-32 H CSNHMe H H H H H H H XVII-33 HOMe H H H H H H H XVII-34 H OEt H H H H H H H XVII-35 H OCOMe H H H H HH H XVII-36 H OCOOMe H H H H H H H XVII-37 H OCONHMe H H H H H H HXVII-38 H OCONMe₂ H H H H H H H XVII-39 H OCSMe H H H H H H H XVII-40 HOCSNMe₂ H H H H H H H XVII-41 H SMe H H H H H H H XVII-42 H SEt H H H HH H H XVII-43 H SCOMe H H H H H H H XVII-44 H SCSNMe₂ H H H H H H HXVII-45 H SCSNHMe H H H H H H H XVII-46 H NHMe H H H H H H H XVII-47 HNH₂ H H H H H H H XVII-48 H NMe₂ H H H H H H H XVII-49 H NHCOMe H H H HH H H XVII-50 H NHCONH₂ H H H H H H H XVII-51 H NHCONHMe H H H H H H HXVII-52 H NHCONMe₂ H H H H H H H XVII-53 H phenyl H H H H H H H XVII-54H 2-chloro- H H H H H H H phenyl XVII-55 H 4-nitrophenyl H H H H H H HXVII-56 H 2-pyridyl H H H H H H H XVII-57 H 3-pyridyl H H H H H H HXVII-58 H 4-pyridyl H H H H H H H XVII-59 H 2-furyl H H H H H H HXVII-60 H PhO H H H H H H H XVII-61 CH₂ H H H H H H H XVII-62 H ═O H H HH H H XVII-63 H ═NOH H H H H H H XVII-64 H ═NOMe H H H H H H XVII-65 H═CH₂ H H H H H H XVII-66 H ═CHMe H H H H H H XVII-67 H H H H H H H H HXVII-68 H H H Me H H H H H XVII-69 H H H Et H H H H H XVII-70 H H Hvinyl H H H H H XVII-71 H H H allyl H H H H H XVII-72 H H H cyclopropylH H H H H XVII-73 H H H F H H H H H XVII-74 H H H Cl H H H H H XVII-75 HH H NO₂ H H H H H XVII-76 H H H CN H H H H H XVII-77 H H H CONH₂ H H H HH XVII-78 H H H CONHMe H H H H H XVII-79 H H H CONMe₂ H H H H H XVII-80H H H COMe H H H H H XVII-81 H H H COOH H H H H H XVII-82 H H H COOMe HH H H H XVII-83 H H H CSOMe H H H H H XVII-84 H H H CSNH₂ H H H H HXVII-85 H H H CSNMe₂ H H H H H XVII-86 H H H CSNHMe H H H H H XVII-87 HH H OMe H H H H H XVII-88 H H H OEt H H H H H XVII-89 H H H OCOMe H H HH H XVII-90 H H H OCOOMe H H H H H XVII-91 H H H OCONHMe H H H H HXVII-92 H H H OCONMe₂ H H H H H XVII-93 H H H OCSMe H H H H H XVII-94 HH H OCSNMe₂ H H H H H XVII-95 H H H SMe H H H H H XVII-96 H H H SEt H HH H H XVII-97 H H H SCOMe H H H H H XVII-98 H H H SCSNMe₂ H H H H HXVII-99 H H H SCSNHMe H H H H H XVII-100 H H H NHMe H H H H H XVII-101 HH H NH₂ H H H H H XVII-102 H H H NMe₂ H H H H H XVII-103 H H H NHCOMe HH H H H XVII-104 H H H NHCONH₂ H H H H H XVII-105 H H H NHCONHMe H H H HH XVII-106 H H H NHCONMe₂ H H H H H XVII-107 H H H phenyl H H H H HXVII-108 H H H 2-chloro- H H H H H phenyl XVII-109 H H H 4- H H H H Hnitrophenyl XVII-110 H H H 2-pyridyl H H H H H XVII-111 H H H 3-pyridylH H H H H XVII-112 H H H 4-pyridyl H H H H H XVII-113 H H H 2-furyl H HH H H XVII-114 H H H PhO H H H H H XVII-115 H H H ═O H H H H XVII-116 HH H ═NOH H H H H XVII-117 H H H ═NOMe H H H H XVII-118 H H H ═CH₂ H H HH XVII-119 H H H ═CHMe H H H H XVII-120 H Me H Me H H H H H XVII-121 HMe F Me H H H H H XVII-122 H Me H F H H H H H XVII-123 H Me F H H H H HH XVII-124 H Me Me H H H H H H XVII-125 H F H Me H H H H H XVII-126 H FH F H H H H H XVII-127 Me H H H H F H H H XVII-128 Et H H H H F H H HXVII-129 vinyl H H H H F H H H XVII-130 allyl H H H H F H H H XVII-131cyclopropyl H H H H F H H H XVII-132 CN H H H H F H H H XVII-133 CONH₂ HH H H F H H H XVII-134 CONHMe H H H H F H H H XVII-135 CONMe₂ H H H H FH H H XVII-136 COMe H H H H F H H H XVII-137 COOH H H H H F H H HXVII-138 COOMe H H H H F H H H XVII-139 CSNHMe H H H H F H H H XVII-140H Me H H H F H H H XVII-141 H Et H H H F H H H XVII-142 H vinyl H H H FH H H XVII-143 H allyl H H H F H H H XVII-144 H cyclopropyl H H H F H HH XVII-145 H F H H H F H H H XVII-146 H Cl H H H F H H H XVII-147 H NO₂H H H F H H H XVII-148 H CN H H H F H H H XVII-149 H CONH₂ H H H F H H HXVII-150 H CONHMe H H H F H H H XVII-151 H CONMe₂ H H H F H H H XVII-152H COMe H H H F H H H XVII-153 H COOH H H H F H H H XVII-154 H COOMe H HH F H H H XVII-155 H CSOMe H H H F H H H XVII-156 H CSNH₂ H H H F H H HXVII-157 H CSNMe₂ H H H F H H H XVII-158 H CSNHMe H H H F H H H XVII-159H OMe H H H F H H H XVII-160 H OEt H H H F H H H XVII-161 H OCOMe H H HF H H H XVII-162 H OCOOMe H H H F H H H XVII-163 H OCONHMe H H H F H H HXVII-164 H OCONMe₂ H H H F H H H XVII-165 H OCSMe H H H F H H H XVII-166H OCSNMe₂ H H H F H H H XVII-167 H SMe H H H F H H H XVII-168 H SEt H HH F H H H XVII-169 H SCOMe H H H F H H H XVII-170 H SCSNMe₂ H H H F H HH XVII-171 H SCSNHMe H H H F H H H XVII-172 H NHMe H H H F H H HXVII-173 H NH₂ H H H F H H H XVII-174 H NMe₂ H H H F H H H XVII-175 HNHCOMe H H H F H H H XVII-176 H NHCONH₂ H H H F H H H XVII-177 HNHCONHMe H H H F H H H XVII-178 H NHCONMe₂ H H H F H H H XVII-179 Hphenyl H H H F H H H XVII-180 H 2-chloro- H H H F H H H phenyl XVII-181H 4-nitrophenyl H H H F H H H XVII-182 H 2-pyridyl H H H F H H HXVII-183 H 3-pyridyl H H H F H H H XVII-184 H 4-pyridyl H H H F H H HXVII-185 H 2-furyl H H H F H H H XVII-186 H PhO H H H F H H H XVII-187CH₂ H H H F H H H XVII-188 H H H Me H F H H H XVII-189 H H H Et H F H HH XVII-190 H H H vinyl H F H H H XVII-191 H H H allyl H F H H H XVII-192H H H cyclopropyl H F H H H XVII-193 H H H F H F H H H XVII-194 H H H ClH F H H H XVII-195 H H H NO₂ H F H H H XVII-196 H H H CN H F H H HXVII-197 H H H CONH₂ H F H H H XVII-198 H H H CONHMe H F H H H XVII-199H H H CONMe₂ H F H H H XVII-200 H H H COMe H F H H H XVII-201 H H H COOHH F H H H XVII-202 H H H COOMe H F H H H XVII-203 H H H CSOMe H F H H HXVII-204 H H H CSNH₂ H F H H H XVII-205 H H H CSNMe₂ H F H H H XVII-206H H H CSNHMe H F H H H XVII-207 H H H OMe H F H H H XVII-208 H H H OEt HF H H H XVII-209 H H H OCOMe H F H H H XVII-210 H H H OCOOMe H F H H HXVII-211 H H H OCONHMe H F H H H XVII-212 H H H OCONMe₂ H F H H HXVII-213 H H H OCSMe H F H H H XVII-214 H H H OCSNMe₂ H F H H H XVII-215H H H SMe H F H H H XVII-216 H H H SEt H F H H H XVII-217 H H H SCOMe HF H H H XVII-218 H H H SCSNMe₂ H F H H H XVII-219 H H H SCSNHMe H F H HH XVII-220 H H H NHMe H F H H H XVII-221 H H H NH₂ H F H H H XVII-222 HH H NMe₂ H F H H H XVII-223 H H H NHCOMe H F H H H XVII-224 H H HNHCONH₂ H F H H H XVII-225 H H H NHCONHMe H F H H H XVII-226 H H HNHCONMe₂ H F H H H XVII-227 H H H phenyl H F H H H XVII-228 H H H2-chloro- H F H H H phenyl XVII-229 H H H 4- H F H H H nitrophenylXVII-230 H H H 2-pyridyl H F H H H XVII-231 H H H 3-pyridyl H F H H HXVII-232 H H H 4-pyridyl H F H H H XVII-233 H H H 2-furyl H F H H HXVII-234 H H H PhO H F H H H XVII-235 H Me H Me H F H H H XVII-236 H MeF Me H F H H H XVII-237 H Me H F H F H H H XVII-238 H Me F H H F H H HXVII-239 H Me Me H H F H H H XVII-240 H F H Me H F H H H XVII-241 H F HF H F H H H XVII-242 Me H H H H Me H H H XVII-243 Et H H H H Me H H HXVII-244 vinyl H H H H Me H H H XVII-245 allyl H H H H Me H H H XVII-246cyclopropyl H H H H Me H H H XVII-247 CN H H H H Me H H H XVII-248 CONH₂H H H H Me H H H XVII-249 CONHMe H H H H Me H H H XVII-250 CONMe₂ H H HH Me H H H XVII-251 COMe H H H H Me H H H XVII-252 COOH H H H H Me H H HXVII-253 COOMe H H H H Me H H H XVII-254 CSNHMe H H H H Me H H HXVII-255 H Me H H H Me H H H XVII-256 H Et H H H Me H H H XVII-257 Hvinyl H H H Me H H H XVII-258 H allyl H H H Me H H H XVII-259 Hcyclopropyl H H H Me H H H XVII-260 H F H H H Me H H H XVII-261 H Cl H HH Me H H H XVII-262 H NO₂ H H H Me H H H XVII-263 H CN H H H Me H H HXVII-264 H CONH₂ H H H Me H H H XVII-265 H CONHMe H H H Me H H HXVII-266 H CONMe₂ H H H Me H H H XVII-267 H COMe H H H Me H H H XVII-268H COOH H H H Me H H H XVII-269 H COOMe H H H Me H H H XVII-270 H CSOMe HH H Me H H H XVII-271 H CSNH₂ H H H Me H H H XVII-272 H CSNMe₂ H H H MeH H H XVII-273 H CSNHMe H H H Me H H H XVII-274 H OMe H H H Me H H HXVII-275 H OEt H H H Me H H H XVII-276 H OCOMe H H H Me H H H XVII-277 HOCOOMe H H H Me H H H XVII-278 H OCONHMe H H H Me H H H XVII-279 HOCONMe₂ H H H Me H H H XVII-280 H OCSMe H H H Me H H H XVII-281 HOCSNMe2 H H H Me H H H XVII-282 H SMe H H H Me H H H XVII-283 H SEt H HH Me H H H XVII-284 H SCOMe H H H Me H H H XVII-285 H SCSNMe₂ H H H Me HH H XVII-286 H SCSNHMe H H H Me H H H XVII-287 H NHMe H H H Me H H HXVII-288 H NH₂ H H H Me H H H XVII-289 H NMe₂ H H H Me H H H XVII-290 HNHCOMe H H H Me H H H XVII-291 H NHCONH₂ H H H Me H H H XVII-292 HNHCONHMe H H H Me H H H XVII-293 H NHCONMe₂ H H H Me H H H XVII-294 Hphenyl H H H Me H H H XVII-295 H 2-chloro- H H H Me H H H phenylXVII-296 H 4-nitrophenyl H H H Me H H H XVII-297 H 2-pyridyl H H H Me HH H XVII-298 H 3-pyridyl H H H Me H H H XVII-299 H 4-pyridyl H H H Me HH H XVII-300 H 2-furyl H H H Me H H H XVII-301 H PhO H H H Me H H HXVII-302 CH₂ H H H Me H H H XVII-303 H H H Me H Me H H H XVII-304 H H HEt H Me H H H XVII-305 H H H vinyl H Me H H H XVII-306 H H H allyl H MeH H H XVII-307 H H H cyclopropyl H Me H H H XVII-308 H H H F H Me H H HXVII-309 H H H Cl H Me H H H XVII-310 H H H NO₂ H Me H H H XVII-311 H HH CN H Me H H H XVII-312 H H H CONH₂ H Me H H H XVII-313 H H H CONHMe HMe H H H XVII-314 H H H CONMe₂ H Me H H H XVII-315 H H H COMe H Me H H HXVII-316 H H H COOH H Me H H H XVII-317 H H H COOMe H Me H H H XVII-318H H H CSOMe H Me H H H XVII-319 H H H CSNH₂ H Me H H H XVII-320 H H HCSNMe₂ H Me H H H XVII-321 H H H CSNHMe H Me H H H XVII-322 H H H OMe HMe H H H XVII-323 H H H OEt H Me H H H XVII-324 H H H OCOMe H Me H H HXVII-325 H H H OCOOMe H Me H H H XVII-326 H H H OCONHMe H Me H H HXVII-327 H H H OCONMe₂ H Me H H H XVII-328 H H H OCSMe H Me H H HXVII-329 H H H OCSNMe2 H Me H H H XVII-330 H H H SMe H Me H H H XVII-331H H H SEt H Me H H H XVII-332 H H H SCOMe H Me H H H XVII-333 H H HSCSNMe₂ H Me H H H XVII-334 H H H SCSNHMe H Me H H H XVII-335 H H H NHMeH Me H H H XVII-336 H H H NH₂ H Me H H H XVII-337 H H H NMe₂ H Me H H HXVII-338 H H H NHCOMe H Me H H H XVII-339 H H H NHCONH₂ H Me H H HXVII-340 H H H NHCONHMe H Me H H H XVII-341 H H H NHCONMe₂ H Me H H HXVII-342 H H H phenyl H Me H H H XVII-343 H H H 2-chloro- H Me H H Hphenyl XVII-344 H H H 4- H Me H H H nitrophenyl XVII-345 H H H 2-pyridylH Me H H H XVII-346 H H H 3-pyridyl H Me H H H XVII-347 H H H 4-pyridylH Me H H H XVII-348 H H H 2-furyl H Me H H H XVII-349 H H H PhO H Me H HH XVII-350 H Me H Me H Me H H H XVII-351 H Me F Me H Me H H H XVII-352 HMe H F H Me H H H XVII-353 H Me F H H Me H H H XVII-354 H Me Me H H Me HH H XVII-355 H F H Me H Me H H H XVII-356 H F H F H Me H H H XVII-357 MeH H H H F H F H XVII-358 Et H H H H F H F H XVII-359 vinyl H H H H F H FH XVII-360 allyl H H H H F H F H XVII-361 cyclopropyl H H H H F H F HXVII-362 CN H H H H F H F H XVII-363 CONH₂ H H H H F H F H XVII-364CONHMe H H H H F H F H XVII-365 CONMe₂ H H H H F H F H XVII-366 COMe H HH H F H F H XVII-367 COOH H H H H F H F H XVII-368 COOMe H H H H F H F HXVII-369 CSNHMe H H H H F H F H XVII-370 H Me H H H F H F H XVII-371 HEt H H H F H F H XVII-372 H vinyl H H H F H F H XVII-373 H allyl H H H FH F H XVII-374 H cyclopropyl H H H F H F H XVII-375 H F H H H F H F HXVII-376 H Cl H H H F H F H XVII-377 H NO₂ H H H F H F H XVII-378 H CN HH H F H F H XVII-379 H CONH₂ H H H F H F H XVII-380 H CONHMe H H H F H FH XVII-381 H CONMe₂ H H H F H F H XVII-382 H COMe H H H F H F H XVII-383H COOH H H H F H F H XVII-384 H COOMe H H H F H F H XVII-385 H CSOMe H HH F H F H XVII-386 H CSNH₂ H H H F H F H XVII-387 H CSNMe₂ H H H F H F HXVII-388 H CSNHMe H H H F H F H XVII-389 H OMe H H H F H F H XVII-390 HOEt H H H F H F H XVII-391 H OCOMe H H H F H F H XVII-392 H OCOOMe H H HF H F H XVII-393 H OCONHMe H H H F H F H XVII-394 H OCONMe₂ H H H F H FH XVII-395 H OCSMe H H H F H F H XVII-396 H OCSNMe2 H H H F H F HXVII-397 H SMe H H H F H F H XVII-398 H SEt H H H F H F H XVII-399 HSCOMe H H H F H F H XVII-400 H SCSNMe₂ H H H F H F H XVII-401 H SCSNHMeH H H F H F H XVII-402 H NHMe H H H F H F H XVII-403 H NH₂ H H H F H F HXVII-404 H NMe₂ H H H F H F H XVII-405 H NHCOMe H H H F H F H XVII-406 HNHCONH₂ H H H F H F H XVII-407 H NHCONHMe H H H F H F H XVII-408 HNHCONMe₂ H H H F H F H XVII-409 H phenyl H H H F H F H XVII-410 H2-chloro- H H H F H F H phenyl XVII-411 H 4-nitrophenyl H H H F H F HXVII-412 H 2-pyridyl H H H F H F H XVII-413 H 3-pyridyl H H H F H F HXVII-414 H 4-pyridyl H H H F H F H XVII-415 H 2-furyl H H H F H F HXVII-416 H PhO H H H F H F H XVII-417 CH₂ H H H F H F H XVII-418 H H HMe H F H F H XVII-419 H H H Et H F H F H XVII-420 H H H vinyl H F H F HXVII-421 H H H allyl H F H F H XVII-422 H H H cyclopropyl H F H F HXVII-423 H H H F H F H F H XVII-424 H H H Cl H F H F H XVII-425 H H HNO₂ H F H F H XVII-426 H H H CN H F H F H XVII-427 H H H CONH₂ H F H F HXVII-428 H H H CONHMe H F H F H XVII-429 H H H CONMe₂ H F H F H XVII-430H H H COMe H F H F H XVII-431 H H H COOH H F H F H XVII-432 H H H COOMeH F H F H XVII-433 H H H CSOMe H F H F H XVII-434 H H H CSNH₂ H F H F HXVII-435 H H H CSNMe₂ H F H F H XVII-436 H H H CSNHMe H F H F H XVII-437H H H OMe H F H F H XVII-438 H H H OEt H F H F H XVII-439 H H H OCOMe HF H F H XVII-440 H H H OCOOMe H F H F H XVII-441 H H H OCONHMe H F H F HXVII-442 H H H OCONMe₂ H F H F H XVII-443 H H H OCSMe H F H F H XVII-444H H H OCSNMe₂ H F H F H XVII-445 H H H SMe H F H F H XVII-446 H H H SEtH F H F H XVII-447 H H H SCOMe H F H F H XVII-448 H H H SCSNMe₂ H F H FH XVII-449 H H H SCSNHMe H F H F H XVII-450 H H H NHMe H F H F HXVII-451 H H H NH₂ H F H F H XVII-452 H H H NMe₂ H F H F H XVII-453 H HH NHCOMe H F H F H XVII-454 H H H NHCONH₂ H F H F H XVII-455 H H HNHCONHMe H F H F H XVII-456 H H H NHCONMe₂ H F H F H XVII-457 H H Hphenyl H F H F H XVII-458 H H H 2-chloro- H F H F H phenyl XVII-459 H HH 4- H F H F H nitrophenyl XVII-460 H H H 2-pyridyl H F H F H XVII-461 HH H 3-pyridyl H F H F H XVII-462 H H H 4-pyridyl H F H F H XVII-463 H HH 2-furyl H F H F H XVII-464 H H H PhO H F H F H XVII-465 H Me H Me H FH F H XVII-466 H Me F Me H F H F H XVII-467 H Me H F H F H F H XVII-468H Me F H H F H F H XVII-469 H Me Me H H F H F H XVII-470 H F H Me H F HF H XVII-471 H F H F H F H F H XVII-472 H H H H H Me H H H XVII-473 H HH H H Et H H H XVII-474 H H H H H vinyl H H H XVII-475 H H H H H allyl HH H XVII-476 H H H H H cyclopropyl H H H XVII-477 H H H H H F H H HXVII-478 H H H H H Cl H H H XVII-479 H H H H H NO₂ H H H XVII-480 H H HH H CN H H H XVII-481 H H H H H CONH₂ H H H XVII-482 H H H H H CONHMe HH H XVII-483 H H H H H CONMe₂ H H H XVII-484 H H H H H COMe H H HXVII-485 H H H H H COOH H H H XVII-486 H H H H H COOMe H H H XVII-487 HH H H H CSOMe H H H XVII-488 H H H H H CSNH₂ H H H XVII-489 H H H H HCSNMe₂ H H H XVII-490 H H H H H CSNHMe H H H XVII-491 H H H H H OMe H HH XVII-492 H H H H H OEt H H H XVII-493 H H H H H OCOMe H H H XVII-494 HH H H H OCOOMe H H H XVII-495 H H H H H OCONHMe H H H XVII-496 H H H H HOCONMe₂ H H H XVII-497 H H H H H OCSMe H H H XVII-498 H H H H H OCSNMe₂H H H XVII-499 H H H H H SMe H H H XVII-500 H H H H H SEt H H H XVII-501H H H H H SCOMe H H H XVII-502 H H H H H SCSNMe₂ H H H XVII-503 H H H HH SCSNHMe H H H XVII-504 H H H H H NHMe H H H XVII-505 H H H H H NH₂ H HH XVII-506 H H H H H NMe₂ H H H XVII-507 H H H H H NHCOMe H H H XVII-508H H H H H NHCONH₂ H H H XVII-509 H H H H H NHCONHMe H H H XVII-510 H H HH H NHCONMe₂ H H H XVII-511 H H H H H phenyl H H H XVII-512 H H H H H 2-H H H chloro- phenyl XVII-513 H H H H H 4- H H H nitrophenyl XVII-514 HH H H H 2- H H H pyridyl XVII-515 H H H H H 3- H H H pyridyl XVII-516 HH H H H 4- H H H pyridyl XVII-517 H H H H H 2-furyl H H H XVII-518 H H HH H PhO H H H XVII-519 H H H H H H H Me H XVII-520 H H H H H H H Et HXVII-521 H H H H H H H vinyl H XVII-522 H H H H H H H allyl H XVII-523 HH H H H H H cyclopropyl H XVII-524 H H H H H H H F H XVII-525 H H H H HH H Cl H XVII-526 H H H H H H H NO₂ H XVII-527 H H H H H H H CN HXVII-528 H H H H H H H CONH₂ H XVII-529 H H H H H H H CONHMe H XVII-530H H H H H H H CONMe₂ H XVII-531 H H H H H H H COMe H XVII-532 H H H H HH H COOH H XVII-533 H H H H H H H COOMe H XVII-534 H H H H H H H CSOMe HXVII-535 H H H H H H H CSNH₂ H XVII-536 H H H H H H H CSNMe₂ H XVII-537H H H H H H H CSNHMe H XVII-538 H H H H H H H OMe H XVII-539 H H H H H HH OEt H XVII-540 H H H H H H H OCOMe H XVII-541 H H H H H H H OCOOMe HXVII-542 H H H H H H H OCONHMe H XVII-543 H H H H H H H OCONMe₂ HXVII-544 H H H H H H H OCSMe H XVII-545 H H H H H H H OCSNMe2 H XVII-546H H H H H H H SMe H XVII-547 H H H H H H H SEt H XVII-548 H H H H H H HSCOMe H XVII-549 H H H H H H H SCSNMe₂ H XVII-550 H H H H H H H SCSNHMeH XVII-551 H H H H H H H NHMe H XVII-552 H H H H H H H NH₂ H XVII-553 HH H H H H H NMe₂ H XVII-554 H H H H H H H NHCOMe H XVII-555 H H H H H HH NHCONH₂ H XVII-556 H H H H H H H NHCONHMe H XVII-557 H H H H H H HNHCONMe₂ H XVII-558 H H H H H H H phenyl H XVII-559 H H H H H H H 2- Hchloro- phenyl XVII-560 H H H H H H H 4- H nitrophenyl XVII-561 H H H HH H H 2- H pyridyl XVII-562 H H H H H H H 3- H pyridyl XVII-563 H H H HH H H 4- H pyridyl XVII-564 H H H H H H H 2-furyl H XVII-565 H H H H H HH PhO H XVII-566 H H H H H H H H Me XVII-567 H H H H H H H H Et XVII-568H H H H H H H H vinyl XVII-569 H H H H H H H H allyl XVII-570 H H H H HH H H cyclopropyl XVII-571 H H H H H H H H F XVII-572 H H H H H H H H ClXVII-573 H H H H H H H H NO₂ XVII-574 H H H H H H H H CN XVII-575 H H HH H H H H CONH₂ XVII-576 H H H H H H H H CONHMe XVII-577 H H H H H H H HCONMe₂ XVII-578 H H H H H H H H COMe XVII-579 H H H H H H H H COOHXVII-580 H H H H H H H H COOMe XVII-581 H H H H H H H H CSOMe XVII-582 HH H H H H H H CSNH₂ XVII-583 H H H H H H H H CSNMe₂ XVII-584 H H H H H HH H CSNHMe XVII-585 H H H H H H H H OMe XVII-586 H H H H H H H H OEtXVII-587 H H H H H H H H OCOMe XVII-588 H H H H H H H H OCOOMe XVII-589H H H H H H H H OCONHMe XVII-590 H H H H H H H H OCONMe₂ XVII-591 H H HH H H H H OCSMe XVII-592 H H H H H H H H OCSNMe2 XVII-593 H H H H H H HH SMe XVII-594 H H H H H H H H SEt XVII-595 H H H H H H H H SCOMeXVII-596 H H H H H H H H SCSNMe₂ XVII-597 H H H H H H H H SCSNHMeXVII-598 H H H H H H H H NHMe XVII-599 H H H H H H H H NH₂ XVII-600 H HH H H H H H NMe₂ XVII-601 H H H H H H H H NHCOMe XVII-602 H H H H H H HH NHCONH₂ XVII-603 H H H H H H H H NHCONHMe XVII-604 H H H H H H H HNHCONMe₂ XVII-605 H H H H H H H H phenyl XVII-606 H H H H H H H H 2-chloro- phenyl XVII-607 H H H H H H H H 4- nitrophenyl XVII-608 H H H HH H H H 2- pyridyl XVII-609 H H H H H H H H 3- pyridyl XVII-610 H H H HH H H H 4- pyridyl XVII-611 H H H H H H H H 2-furyl XVII-612 H H H H H HH H PhO

Table XVIII provides 612 compounds of formula Ir

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4a), R⁵, R⁶ andR⁹ are given in Table 2.

Table XIX provides 612 compounds of formula Is

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XX provides 612 compounds of formula It

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXI provides 612 compounds of formula Iu

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXII provides 612 compounds of formula Iv

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXIII provides 612 compounds of formula Iw

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXIV provides 612 compounds of formula Ix

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXV provides 612 compounds of formula Iy

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXVI provides 612 compounds of formula Iz

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 2.

Table XXVII provides 612 compounds of formula Iaa

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 3.

TABLE 3 Compound No R9 R1 R2 R5 R6 R4a R4b R4c R4d XXVII-1 Me H H H H HH H H XXVII-2 Et H H H H H H H H XXVII-3 vinyl H H H H H H H H XXVII-4allyl H H H H H H H H XXVII-5 cyclopropyl H H H H H H H H XXVII-6 CN H HH H H H H H XXVII-7 CONH₂ H H H H H H H H XXVII-8 CONHMe H H H H H H H HXXVII-9 CONMe₂ H H H H H H H H XXVII-10 COMe H H H H H H H H XXVII-11COOH H H H H H H H H XXVII-12 COOMe H H H H H H H H XXVII-13 CSNHMe H HH H H H H H XXVII-14 H Me H H H H H H H XXVII-15 H Et H H H H H H HXXVII-16 H vinyl H H H H H H H XXVII-17 H allyl H H H H H H H XXVII-18 Hcyclopropyl H H H H H H H XXVII-19 H F H H H H H H H XXVII-20 H Cl H H HH H H H XXVII-21 H NO₂ H H H H H H H XXVII-22 H CN H H H H H H HXXVII-23 H CONH₂ H H H H H H H XXVII-24 H CONHMe H H H H H H H XXVII-25H CONMe₂ H H H H H H H XXVII-26 H COMe H H H H H H H XXVII-27 H COOH H HH H H H H XXVII-28 H COOMe H H H H H H H XXVII-29 H CSOMe H H H H H H HXXVII-30 H CSNH₂ H H H H H H H XXVII-31 H CSNMe₂ H H H H H H H XXVII-32H CSNHMe H H H H H H H XXVII-33 H OMe H H H H H H H XXVII-34 H OEt H H HH H H H XXVII-35 H OCOMe H H H H H H H XXVII-36 H OCOOMe H H H H H H HXXVII-37 H OCONHMe H H H H H H H XXVII-38 H OCONMe₂ H H H H H H HXXVII-39 H OCSMe H H H H H H H XXVII-40 H OCSNMe2 H H H H H H H XXVII-41H SMe H H H H H H H XXVII-42 H SEt H H H H H H H XXVII-43 H SCOMe H H HH H H H XXVII-44 H SCSNMe₂ H H H H H H H XXVII-45 H SCSNHMe H H H H H HH XXVII-46 H NHMe H H H H H H H XXVII-47 H NH₂ H H H H H H H XXVII-48 HNMe₂ H H H H H H H XXVII-49 H NHCOMe H H H H H H H XXVII-50 H NHCONH₂ HH H H H H H XXVII-51 H NHCONHMe H H H H H H H XXVII-52 H NHCONMe₂ H H HH H H H XXVII-53 H phenyl H H H H H H H XXVII-54 H 2- H H H H H H Hchloro- phenyl XXVII-55 H 4- H H H H H H H nitrophenyl XXVII-56 H 2- H HH H H H H pyridyl XXVII-57 H 3- H H H H H H H pyridyl XXVII-58 H 4- H HH H H H H pyridyl XXVII-59 H 2-furyl H H H H H H H XXVII-60 H PhO H H HH H H H XXVII-61 CH₂ H H H H H H H XXVII-62 H ═O H H H H H H XXVII-63 H═NOH H H H H H H XXVII-64 H ═NOMe H H H H H H XXVII-65 H ═CH₂ H H H H HH XXVII-66 H ═CHMe H H H H H H XXVII-67 H H H H H H H H H XXVII-68 H H HMe H H H H H XXVII-69 H H H Et H H H H H XXVII-70 H H H vinyl H H H H HXXVII-71 H H H allyl H H H H H XXVII-72 H H H cyclopropyl H H H H HXXVII-73 H H H F H H H H H XXVII-74 H H H Cl H H H H H XXVII-75 H H HNO₂ H H H H H XXVII-76 H H H CN H H H H H XXVII-77 H H H CONH₂ H H H H HXXVII-78 H H H CONHMe H H H H H XXVII-79 H H H CONMe₂ H H H H H XXVII-80H H H COMe H H H H H XXVII-81 H H H COOH H H H H H XXVII-82 H H H COOMeH H H H H XXVII-83 H H H CSOMe H H H H H XXVII-84 H H H CSNH₂ H H H H HXXVII-85 H H H CSNMe₂ H H H H H XXVII-86 H H H CSNHMe H H H H H XXVII-87H H H OMe H H H H H XXVII-88 H H H OEt H H H H H XXVII-89 H H H OCOMe HH H H H XXVII-90 H H H OCOOMe H H H H H XXVII-91 H H H OCONHMe H H H H HXXVII-92 H H H OCONMe₂ H H H H H XXVII-93 H H H OCSMe H H H H H XXVII-94H H H OCSNMe2 H H H H H XXVII-95 H H H SMe H H H H H XXVII-96 H H H SEtH H H H H XXVII-97 H H H SCOMe H H H H H XXVII-98 H H H SCSNMe₂ H H H HH XXVII-99 H H H SCSNHMe H H H H H XXVII-100 H H H NHMe H H H H HXXVII-101 H H H NH₂ H H H H H XXVII-102 H H H NMe₂ H H H H H XXVII-103 HH H NHCOMe H H H H H XXVII-104 H H H NHCONH₂ H H H H H XXVII-105 H H HNHCONHMe H H H H H XXVII-106 H H H NHCONMe₂ H H H H H XXVII-107 H H Hphenyl H H H H H XXVII-108 H H H 2- H H H H H chloro- phenyl XXVII-109 HH H 4- H H H H H nitrophenyl XXVII-110 H H H 2- H H H H H pyridylXXVII-111 H H H 3- H H H H H pyridyl XXVII-112 H H H 4- H H H H Hpyridyl XXVII-113 H H H 2-furyl H H H H H XXVII-114 H H H PhO H H H H HXXVII-115 H H H ═O H H H H XXVII-116 H H H ═NOH H H H H XXVII-117 H H H═NOMe H H H H XXVII-118 H H H ═CH₂ H H H H XXVII-119 H H H ═CHMe H H H HXXVII-120 H Me H Me H H H H H XXVII-121 H Me F Me H H H H H XXVII-122 HMe H F H H H H H XXVII-123 H Me F H H H H H H XXVII-124 H Me Me H H H HH H XXVII-125 H F H Me H H H H H XXVII-126 H F H F H H H H H XXVII-127Me H H H H F H H H XXVII-128 Et H H H H F H H H XXVII-129 vinyl H H H HF H H H XXVII-130 allyl H H H H F H H H XXVII-131 cyclopropyl H H H H FH H H XXVII-132 CN H H H H F H H H XXVII-133 CONH₂ H H H H F H H HXXVII-134 CONHMe H H H H F H H H XXVII-135 CONMe₂ H H H H F H H HXXVII-136 COMe H H H H F H H H XXVII-137 COOH H H H H F H H H XXVII-138COOMe H H H H F H H H XXVII-139 CSNHMe H H H H F H H H XXVII-140 H Me HH H F H H H XXVII-141 H Et H H H F H H H XXVII-142 H vinyl H H H F H H HXXVII-143 H allyl H H H F H H H XXVII-144 H cyclopropyl H H H F H H HXXVII-145 H F H H H F H H H XXVII-146 H Cl H H H F H H H XXVII-147 H NO₂H H H F H H H XXVII-148 H CN H H H F H H H XXVII-149 H CONH₂ H H H F H HH XXVII-150 H CONHMe H H H F H H H XXVII-151 H CONMe₂ H H H F H H HXXVII-152 H COMe H H H F H H H XXVII-153 H COOH H H H F H H H XXVII-154H COOMe H H H F H H H XXVII-155 H CSOMe H H H F H H H XXVII-156 H CSNH₂H H H F H H H XXVII-157 H CSNMe₂ H H H F H H H XXVII-158 H CSNHMe H H HF H H H XXVII-159 H OMe H H H F H H H XXVII-160 H OEt H H H F H H HXXVII-161 H OCOMe H H H F H H H XXVII-162 H OCOOMe H H H F H H HXXVII-163 H OCONHMe H H H F H H H XXVII-164 H OCONMe₂ H H H F H H HXXVII-165 H OCSMe H H H F H H H XXVII-166 H OCSNMe2 H H H F H H HXXVII-167 H SMe H H H F H H H XXVII-168 H SEt H H H F H H H XXVII-169 HSCOMe H H H F H H H XXVII-170 H SCSNMe₂ H H H F H H H XXVII-171 HSCSNHMe H H H F H H H XXVII-172 H NHMe H H H F H H H XXVII-173 H NH₂ H HH F H H H XXVII-174 H NMe₂ H H H F H H H XXVII-175 H NHCOMe H H H F H HH XXVII-176 H NHCONH₂ H H H F H H H XXVII-177 H NHCONHMe H H H F H H HXXVII-178 H NHCONMe₂ H H H F H H H XXVII-179 H phenyl H H H F H H HXXVII-180 H 2- H H H F H H H chloro- phenyl XXVII-181 H 4- H H H F H H Hnitrophenyl XXVII-182 H 2- H H H F H H H pyridyl XXVII-183 H 3- H H H FH H H pyridyl XXVII-184 H 4- H H H F H H H pyridyl XXVII-185 H 2-furyl HH H F H H H XXVII-186 H PhO H H H F H H H XXVII-187 CH₂ H H H F H H HXXVII-188 H H H Me H F H H H XXVII-189 H H H Et H F H H H XXVII-190 H HH vinyl H F H H H XXVII-191 H H H allyl H F H H H XXVII-192 H H Hcyclopropyl H F H H H XXVII-193 H H H F H F H H H XXVII-194 H H H Cl H FH H H XXVII-195 H H H NO₂ H F H H H XXVII-196 H H H CN H F H H HXXVII-197 H H H CONH₂ H F H H H XXVII-198 H H H CONHMe H F H H HXXVII-199 H H H CONMe₂ H F H H H XXVII-200 H H H COMe H F H H HXXVII-201 H H H COOH H F H H H XXVII-202 H H H COOMe H F H H H XXVII-203H H H CSOMe H F H H H XXVII-204 H H H CSNH₂ H F H H H XXVII-205 H H HCSNMe₂ H F H H H XXVII-206 H H H CSNHMe H F H H H XXVII-207 H H H OMe HF H H H XXVII-208 H H H OEt H F H H H XXVII-209 H H H OCOMe H F H H HXXVII-210 H H H OCOOMe H F H H H XXVII-211 H H H OCONHMe H F H H HXXVII-212 H H H OCONMe₂ H F H H H XXVII-213 H H H OCSMe H F H H HXXVII-214 H H H OCSNMe2 H F H H H XXVII-215 H H H SMe H F H H HXXVII-216 H H H SEt H F H H H XXVII-217 H H H SCOMe H F H H H XXVII-218H H H SCSNMe₂ H F H H H XXVII-219 H H H SCSNHMe H F H H H XXVII-220 H HH NHMe H F H H H XXVII-221 H H H NH₂ H F H H H XXVII-222 H H H NMe₂ H FH H H XXVII-223 H H H NHCOMe H F H H H XXVII-224 H H H NHCONH₂ H F H H HXXVII-225 H H H NHCONHMe H F H H H XXVII-226 H H H NHCONMe₂ H F H H HXXVII-227 H H H phenyl H F H H H XXVII-228 H H H 2- H F H H H chloro-phenyl XXVII-229 H H H 4- H F H H H nitrophenyl XXVII-230 H H H 2- H F HH H pyridyl XXVII-231 H H H 3- H F H H H pyridyl XXVII-232 H H H 4- H FH H H pyridyl XXVII-233 H H H 2-furyl H F H H H XXVII-234 H H H PhO H FH H H XXVII-235 H Me H Me H F H H H XXVII-236 H Me F Me H F H H HXXVII-237 H Me H F H F H H H XXVII-238 H Me F H H F H H H XXVII-239 H MeMe H H F H H H XXVII-240 H F H Me H F H H H XXVII-241 H F H F H F H H HXXVII-242 Me H H H H Me H H H XXVII-243 Et H H H H Me H H H XXVII-244vinyl H H H H Me H H H XXVII-245 allyl H H H H Me H H H XXVII-246cyclopropyl H H H H Me H H H XXVII-247 CN H H H H Me H H H XXVII-248CONH₂ H H H H Me H H H XXVII-249 CONHMe H H H H Me H H H XXVII-250CONMe₂ H H H H Me H H H XXVII-251 COMe H H H H Me H H H XXVII-252 COOH HH H H Me H H H XXVII-253 COOMe H H H H Me H H H XXVII-254 CSNHMe H H H HMe H H H XXVII-255 H Me H H H Me H H H XXVII-256 H Et H H H Me H H HXXVII-257 H vinyl H H H Me H H H XXVII-258 H allyl H H H Me H H HXXVII-259 H cyclopropyl H H H Me H H H XXVII-260 H F H H H Me H H HXXVII-261 H Cl H H H Me H H H XXVII-262 H NO₂ H H H Me H H H XXVII-263 HCN H H H Me H H H XXVII-264 H CONH₂ H H H Me H H H XXVII-265 H CONHMe HH H Me H H H XXVII-266 H CONMe₂ H H H Me H H H XXVII-267 H COMe H H H MeH H H XXVII-268 H COOH H H H Me H H H XXVII-269 H COOMe H H H Me H H HXXVII-270 H CSOMe H H H Me H H H XXVII-271 H CSNH₂ H H H Me H H HXXVII-272 H CSNMe₂ H H H Me H H H XXVII-273 H CSNHMe H H H Me H H HXXVII-274 H OMe H H H Me H H H XXVII-275 H OEt H H H Me H H H XXVII-276H OCOMe H H H Me H H H XXVII-277 H OCOOMe H H H Me H H H XXVII-278 HOCONHMe H H H Me H H H XXVII-279 H OCONMe₂ H H H Me H H H XXVII-280 HOCSMe H H H Me H H H XXVII-281 H OCSNMe₂ H H H Me H H H XXVII-282 H SMeH H H Me H H H XXVII-283 H SEt H H H Me H H H XXVII-284 H SCOMe H H H MeH H H XXVII-285 H SCSNMe₂ H H H Me H H H XXVII-286 H SCSNHMe H H H Me HH H XXVII-287 H NHMe H H H Me H H H XXVII-288 H NH₂ H H H Me H H HXXVII-289 H NMe₂ H H H Me H H H XXVII-290 H NHCOMe H H H Me H H HXXVII-291 H NHCONH₂ H H H Me H H H XXVII-292 H NHCONHMe H H H Me H H HXXVII-293 H NHCONMe₂ H H H Me H H H XXVII-294 H phenyl H H H Me H H HXXVII-295 H 2- H H H Me H H H chloro- phenyl XXVII-296 H 4- H H H Me H HH nitrophenyl XXVII-297 H 2- H H H Me H H H pyridyl XXVII-298 H 3- H H HMe H H H pyridyl XXVII-299 H 4- H H H Me H H H pyridyl XXVII-300 H2-furyl H H H Me H H H XXVII-301 H PhO H H H Me H H H XXVII-302 CH₂ H HH Me H H H XXVII-303 H H H Me H Me H H H XXVII-304 H H H Et H Me H H HXXVII-305 H H H vinyl H Me H H H XXVII-306 H H H allyl H Me H H HXXVII-307 H H H cyclopropyl H Me H H H XXVII-308 H H H F H Me H H HXXVII-309 H H H Cl H Me H H H XXVII-310 H H H NO₂ H Me H H H XXVII-311 HH H CN H Me H H H XXVII-312 H H H CONH₂ H Me H H H XXVII-313 H H HCONHMe H Me H H H XXVII-314 H H H CONMe₂ H Me H H H XXVII-315 H H H COMeH Me H H H XXVII-316 H H H COOH H Me H H H XXVII-317 H H H COOMe H Me HH H XXVII-318 H H H CSOMe H Me H H H XXVII-319 H H H CSNH₂ H Me H H HXXVII-320 H H H CSNMe₂ H Me H H H XXVII-321 H H H CSNHMe H Me H H HXXVII-322 H H H OMe H Me H H H XXVII-323 H H H OEt H Me H H H XXVII-324H H H OCOMe H Me H H H XXVII-325 H H H OCOOMe H Me H H H XXVII-326 H H HOCONHMe H Me H H H XXVII-327 H H H OCONMe₂ H Me H H H XXVII-328 H H HOCSMe H Me H H H XXVII-329 H H H OCSNMe₂ H Me H H H XXVII-330 H H H SMeH Me H H H XXVII-331 H H H SEt H Me H H H XXVII-332 H H H SCOMe H Me H HH XXVII-333 H H H SCSNMe₂ H Me H H H XXVII-334 H H H SCSNHMe H Me H H HXXVII-335 H H H NHMe H Me H H H XXVII-336 H H H NH₂ H Me H H H XXVII-337H H H NMe₂ H Me H H H XXVII-338 H H H NHCOMe H Me H H H XXVII-339 H H HNHCONH₂ H Me H H H XXVII-340 H H H NHCONHMe H Me H H H XXVII-341 H H HNHCONMe₂ H Me H H H XXVII-342 H H H phenyl H Me H H H XXVII-343 H H H 2-H Me H H H chloro- phenyl XXVII-344 H H H 4- H Me H H H nitrophenylXXVII-345 H H H 2- H Me H H H pyridyl XXVII-346 H H H 3- H Me H H Hpyridyl XXVII-347 H H H 4- H Me H H H pyridyl XXVII-348 H H H 2-furyl HMe H H H XXVII-349 H H H PhO H Me H H H XXVII-350 H Me H Me H Me H H HXXVII-351 H Me F Me H Me H H H XXVII-352 H Me H F H Me H H H XXVII-353 HMe F H H Me H H H XXVII-354 H Me Me H H Me H H H XXVII-355 H F H Me H MeH H H XXVII-356 H F H F H Me H H H XXVII-357 Me H H H H F H F HXXVII-358 Et H H H H F H F H XXVII-359 vinyl H H H H F H F H XXVII-360allyl H H H H F H F H XXVII-361 cyclopropyl H H H H F H F H XXVII-362 CNH H H H F H F H XXVII-363 CONH₂ H H H H F H F H XXVII-364 CONHMe H H H HF H F H XXVII-365 CONMe₂ H H H H F H F H XXVII-366 COMe H H H H F H F HXXVII-367 COOH H H H H F H F H XXVII-368 COOMe H H H H F H F H XXVII-369CSNHMe H H H H F H F H XXVII-370 H Me H H H F H F H XXVII-371 H Et H H HF H F H XXVII-372 H vinyl H H H F H F H XXVII-373 H allyl H H H F H F HXXVII-374 H cyclopropyl H H H F H F H XXVII-375 H F H H H F H F HXXVII-376 H Cl H H H F H F H XXVII-377 H NO₂ H H H F H F H XXVII-378 HCN H H H F H F H XXVII-379 H CONH₂ H H H F H F H XXVII-380 H CONHMe H HH F H F H XXVII-381 H CONMe₂ H H H F H F H XXVII-382 H COMe H H H F H FH XXVII-383 H COOH H H H F H F H XXVII-384 H COOMe H H H F H F HXXVII-385 H CSOMe H H H F H F H XXVII-386 H CSNH₂ H H H F H F HXXVII-387 H CSNMe₂ H H H F H F H XXVII-388 H CSNHMe H H H F H F HXXVII-389 H OMe H H H F H F H XXVII-390 H OEt H H H F H F H XXVII-391 HOCOMe H H H F H F H XXVII-392 H OCOOMe H H H F H F H XXVII-393 H OCONHMeH H H F H F H XXVII-394 H OCONMe₂ H H H F H F H XXVII-395 H OCSMe H H HF H F H XXVII-396 H OCSNMe₂ H H H F H F H XXVII-397 H SMe H H H F H F HXXVII-398 H SEt H H H F H F H XXVII-399 H SCOMe H H H F H F H XXVII-400H SCSNMe₂ H H H F H F H XXVII-401 H SCSNHMe H H H F H F H XXVII-402 HNHMe H H H F H F H XXVII-403 H NH₂ H H H F H F H XXVII-404 H NMe₂ H H HF H F H XXVII-405 H NHCOMe H H H F H F H XXVII-406 H NHCONH₂ H H H F H FH XXVII-407 H NHCONHMe H H H F H F H XXVII-408 H NHCONMe₂ H H H F H F HXXVII-409 H phenyl H H H F H F H XXVII-410 H 2- H H H F H F H chloro-phenyl XXVII-411 H 4- H H H F H F H nitrophenyl XXVII-412 H 2- H H H F HF H pyridyl XXVII-413 H 3- H H H F H F H pyridyl XXVII-414 H 4- H H H FH F H pyridyl XXVII-415 H 2-furyl H H H F H F H XXVII-416 H PhO H H H FH F H XXVII-417 CH₂ H H H F H F H XXVII-418 H H H Me H F H F H XXVII-419H H H Et H F H F H XXVII-420 H H H vinyl H F H F H XXVII-421 H H H allylH F H F H XXVII-422 H H H cyclopropyl H F H F H XXVII-423 H H H F H F HF H XXVII-424 H H H Cl H F H F H XXVII-425 H H H NO₂ H F H F H XXVII-426H H H CN H F H F H XXVII-427 H H H CONH₂ H F H F H XXVII-428 H H HCONHMe H F H F H XXVII-429 H H H CONMe₂ H F H F H XXVII-430 H H H COMe HF H F H XXVII-431 H H H COOH H F H F H XXVII-432 H H H COOMe H F H F HXXVII-433 H H H CSOMe H F H F H XXVII-434 H H H CSNH₂ H F H F HXXVII-435 H H H CSNMe₂ H F H F H XXVII-436 H H H CSNHMe H F H F HXXVII-437 H H H OMe H F H F H XXVII-438 H H H OEt H F H F H XXVII-439 HH H OCOMe H F H F H XXVII-440 H H H OCOOMe H F H F H XXVII-441 H H HOCONHMe H F H F H XXVII-442 H H H OCONMe₂ H F H F H XXVII-443 H H HOCSMe H F H F H XXVII-444 H H H OCSNMe2 H F H F H XXVII-445 H H H SMe HF H F H XXVII-446 H H H SEt H F H F H XXVII-447 H H H SCOMe H F H F HXXVII-448 H H H SCSNMe₂ H F H F H XXVII-449 H H H SCSNHMe H F H F HXXVII-450 H H H NHMe H F H F H XXVII-451 H H H NH₂ H F H F H XXVII-452 HH H NMe₂ H F H F H XXVII-453 H H H NHCOMe H F H F H XXVII-454 H H HNHCONH₂ H F H F H XXVII-455 H H H NHCONHMe H F H F H XXVII-456 H H HNHCONMe₂ H F H F H XXVII-457 H H H phenyl H F H F H XXVII-458 H H H 2- HF H F H chloro- phenyl XXVII-459 H H H 4- H F H F H nitrophenylXXVII-460 H H H 2- H F H F H pyridyl XXVII-461 H H H 3- H F H F Hpyridyl XXVII-462 H H H 4- H F H F H pyridyl XXVII-463 H H H 2-furyl H FH F H XXVII-464 H H H PhO H F H F H XXVII-465 H Me H Me H F H F HXXVII-466 H Me F Me H F H F H XXVII-467 H Me H F H F H F H XXVII-468 HMe F H H F H F H XXVII-469 H Me Me H H F H F H XXVII-470 H F H Me H F HF H XXVII-471 H F H F H F H F H XXVII-472 H H H H H Me H H H XXVII-473 HH H H H Et H H H XXVII-474 H H H H H vinyl H H H XXVII-475 H H H H Hallyl H H H XXVII-476 H H H H H cyclopropyl H H H XXVII-477 H H H H H FH H H XXVII-478 H H H H H Cl H H H XXVII-479 H H H H H NO₂ H H HXXVII-480 H H H H H CN H H H XXVII-481 H H H H H CONH₂ H H H XXVII-482 HH H H H CONHMe H H H XXVII-483 H H H H H CONMe₂ H H H XXVII-484 H H H HH COMe H H H XXVII-485 H H H H H COOH H H H XXVII-486 H H H H H COOMe HH H XXVII-487 H H H H H CSOMe H H H XXVII-488 H H H H H CSNH₂ H H HXXVII-489 H H H H H CSNMe₂ H H H XXVII-490 H H H H H CSNHMe H H HXXVII-491 H H H H H OMe H H H XXVII-492 H H H H H OEt H H H XXVII-493 HH H H H OCOMe H H H XXVII-494 H H H H H OCOOMe H H H XXVII-495 H H H H HOCONHMe H H H XXVII-496 H H H H H OCONMe₂ H H H XXVII-497 H H H H HOCSMe H H H XXVII-498 H H H H H OCSNMe2 H H H XXVII-499 H H H H H SMe HH H XXVII-500 H H H H H SEt H H H XXVII-501 H H H H H SCOMe H H HXXVII-502 H H H H H SCSNMe₂ H H H XXVII-503 H H H H H SCSNHMe H H HXXVII-504 H H H H H NHMe H H H XXVII-505 H H H H H NH₂ H H H XXVII-506 HH H H H NMe₂ H H H XXVII-507 H H H H H NHCOMe H H H XXVII-508 H H H H HNHCONH₂ H H H XXVII-509 H H H H H NHCONHMe H H H XXVII-510 H H H H HNHCONMe₂ H H H XXVII-511 H H H H H phenyl H H H XXVII-512 H H H H H 2- HH H chloro- phenyl XXVII-513 H H H H H 4- H H H nitrophenyl XXVII-514 HH H H H 2- H H H pyridyl XXVII-515 H H H H H 3- H H H pyridyl XXVII-516H H H H H 4- H H H pyridyl XXVII-517 H H H H H 2-furyl H H H XXVII-518 HH H H H PhO H H H XXVII-519 H H H H H H H Me H XXVII-520 H H H H H H HEt H XXVII-521 H H H H H H H vinyl H XXVII-522 H H H H H H H allyl HXXVII-523 H H H H H H H cyclopropyl H XXVII-524 H H H H H H H F HXXVII-525 H H H H H H H Cl H XXVII-526 H H H H H H H NO₂ H XXVII-527 H HH H H H H CN H XXVII-528 H H H H H H H CONH₂ H XXVII-529 H H H H H H HCONHMe H XXVII-530 H H H H H H H CONMe₂ H XXVII-531 H H H H H H H COMe HXXVII-532 H H H H H H H COOH H XXVII-533 H H H H H H H COOMe H XXVII-534H H H H H H H CSOMe H XXVII-535 H H H H H H H CSNH₂ H XXVII-536 H H H HH H H CSNMe₂ H XXVII-537 H H H H H H H CSNHMe H XXVII-538 H H H H H H HOMe H XXVII-539 H H H H H H H OEt H XXVII-540 H H H H H H H OCOMe HXXVII-541 H H H H H H H OCOOMe H XXVII-542 H H H H H H H OCONHMe HXXVII-543 H H H H H H H OCONMe₂ H XXVII-544 H H H H H H H OCSMe HXXVII-545 H H H H H H H OCSNMe2 H XXVII-546 H H H H H H H SMe HXXVII-547 H H H H H H H SEt H XXVII-548 H H H H H H H SCOMe H XXVII-549H H H H H H H SCSNMe₂ H XXVII-550 H H H H H H H SCSNHMe H XXVII-551 H HH H H H H NHMe H XXVII-552 H H H H H H H NH₂ H XXVII-553 H H H H H H HNMe₂ H XXVII-554 H H H H H H H NHCOMe H XXVII-555 H H H H H H H NHCONH₂H XXVII-556 H H H H H H H NHCONHMe H XXVII-557 H H H H H H H NHCONMe₂ HXXVII-558 H H H H H H H phenyl H XXVII-559 H H H H H H H 2-chloro-phenylH XXVII-560 H H H H H H H 4-nitrophenyl H XXVII-561 H H H H H H H2-pyridyl H XXVII-562 H H H H H H H 3-pyridyl H XXVII-563 H H H H H H H4-pyridyl H XXVII-564 H H H H H H H 2-furyl H XXVII-565 H H H H H H HPhO H XXVII-566 H H H H H H H H Me XXVII-567 H H H H H H H H EtXXVII-568 H H H H H H H H vinyl XXVII-569 H H H H H H H H allylXXVII-570 H H H H H H H H cyclopropyl XXVII-571 H H H H H H H H FXXVII-572 H H H H H H H H Cl XXVII-573 H H H H H H H H NO₂ XXVII-574 H HH H H H H H CN XXVII-575 H H H H H H H H CONH₂ XXVII-576 H H H H H H H HCONHMe XXVII-577 H H H H H H H H CONMe₂ XXVII-578 H H H H H H H H COMeXXVII-579 H H H H H H H H COOH XXVII-580 H H H H H H H H COOMe XXVII-581H H H H H H H H CSOMe XXVII-582 H H H H H H H H CSNH₂ XXVII-583 H H H HH H H H CSNMe₂ XXVII-584 H H H H H H H H CSNHMe XXVII-585 H H H H H H HH OMe XXVII-586 H H H H H H H H OEt XXVII-587 H H H H H H H H OCOMeXXVII-588 H H H H H H H H OCOOMe XXVII-589 H H H H H H H H OCONHMeXXVII-590 H H H H H H H H OCONMe₂ XXVII-591 H H H H H H H H OCSMeXXVII-592 H H H H H H H H OCSNMe₂ XXVII-593 H H H H H H H H SMeXXVII-594 H H H H H H H H SEt XXVII-595 H H H H H H H H SCOMe XXVII-596H H H H H H H H SCSNMe₂ XXVII-597 H H H H H H H H SCSNHMe XXVII-598 H HH H H H H H NHMe XXVII-599 H H H H H H H H NH₂ XXVII-600 H H H H H H H HNMe₂ XXVII-601 H H H H H H H H NHCOMe XXVII-602 H H H H H H H H NHCONH₂XXVII-603 H H H H H H H H NHCONHMe XXVII-604 H H H H H H H H NHCONMe₂XXVII-605 H H H H H H H H phenyl XXVII-606 H H H H H H H H 2-chloro-phenyl XXVII-607 H H H H H H H H 4- nitrophenyl XXVII-608 H H H H H H HH 2-pyridyl XXVII-609 H H H H H H H H 3-pyridyl XXVII-610 H H H H H H HH 4-pyridyl XXVII-611 H H H H H H H H 2-furyl XXVII-612 H H H H H H H HPhO

Table XXVIII provides 422 compounds of formula Iab

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4

TABLE 4 Compound No R9 R1 R2 R4a R4b R4c R4d XXVIII-1 Me H H H H H HXXVIII-2 Et H H H H H H XXVIII-3 vinyl H H H H H H XXVIII-4 allyl H H HH H H XXVIII-5 cyclopropyl H H H H H H XXVIII-6 CN H H H H H H XXVIII-7CONH₂ H H H H H H XXVIII-8 CONHMe H H H H H H XXVIII-9 CONMe₂ H H H H HH XXVIII-10 COMe H H H H H H XXVIII-11 COOH H H H H H H XXVIII-12 COOMeH H H H H H XXVIII-13 CSNHMe H H H H H H XXVIII-14 H Me H H H H HXXVIII-15 H Et H H H H H XXVIII-16 H Vinyl H H H H H XXVIII-17 H Allyl HH H H H XXVIII-18 H Cyclopropyl H H H H H XXVIII-19 H F H H H H HXXVIII-20 H Cl H H H H H XXVIII-21 H NO₂ H H H H H XXVIII-22 H CN H H HH H XXVIII-23 H CONH₂ H H H H H XXVIII-24 H CONHMe H H H H H XXVIII-25 HCONMe₂ H H H H H XXVIII-26 H COMe H H H H H XXVIII-27 H COOH H H H H HXXVIII-28 H COOMe H H H H H XXVIII-29 H CSOMe H H H H H XXVIII-30 HCSNH₂ H H H H H XXVIII-31 H CSNMe₂ H H H H H XXVIII-32 H CSNHMe H H H HH XXVIII-33 H OMe H H H H H XXVIII-34 H OEt H H H H H XXVIII-35 H OCOMeH H H H H XXVIII-36 H OCOOMe H H H H H XXVIII-37 H OCONHMe H H H H HXXVIII-38 H OCONMe₂ H H H H H XXVIII-39 H OCSMe H H H H H XXVIII-40 HOCSNMe₂ H H H H H XXVIII-41 H SMe H H H H H XXVIII-42 H SEt H H H H HXXVIII-43 H SCOMe H H H H H XXVIII-44 H SCSNMe₂ H H H H H XXVIII-45 HSCSNHMe H H H H H XXVIII-46 H NHMe H H H H H XXVIII-47 H NH₂ H H H H HXXVIII-48 H NMe₂ H H H H H XXVIII-49 H NHCOMe H H H H H XXVIII-50 HNHCONH₂ H H H H H XXVIII-51 H NHCONHMe H H H H H XXVIII-52 H NHCONMe₂ HH H H H XXVIII-53 H Phenyl H H H H H XXVIII-54 H 2-chloro- H H H H Hphenyl XXVIII-55 H 4-nitrophenyl H H H H H XXVIII-56 H 2-pyridyl H H H HH XXVIII-57 H 3-pyridyl H H H H H XXVIII-58 H 4-pyridyl H H H H HXXVIII-59 H 2-furyl H H H H H XXVIII-60 H PhO H H H H H XXVIII-61 CH₂ HH H H H XXVIII-62 H ═O H H H H XXVIII-63 H ═NOH H H H H XXVIII-64 H═NOMe H H H H XXVIII-65 H ═CH₂ H H H H XXVIII-66 H ═CHMe H H H HXXVIII-67 H H H H H H H XXVIII-68 H Me H H H H H XXVIII-69 H Me F H H HH XXVIII-70 H Et H H H H H XXVIII-71 H Me Me H H H H XXVIII-72 Me H Me HH H H XXVIII-73 H F H H H H H XXVIII-74 Me F H H H H H XXVIII-75 Me H HF H H H XXVIII-76 Et H H F H H H XXVIII-77 vinyl H H F H H H XXVIII-78allyl H H F H H H XXVIII-79 cyclopropyl H H F H H H XXVIII-80 CN H H F HH H XXVIII-81 CONH₂ H H F H H H XXVIII-82 CONHMe H H F H H H XXVIII-83CONMe₂ H H F H H H XXVIII-84 COMe H H F H H H XXVIII-85 COOH H H F H H HXXVIII-86 COOMe H H F H H H XXVIII-87 CSNHMe H H F H H H XXVIII-88 H MeH F H H H XXVIII-89 H Et H F H H H XXVIII-90 H vinyl H F H H H XXVIII-91H allyl H F H H H XXVIII-92 H cyclopropyl H F H H H XXVIII-93 H F H F HH H XXVIII-94 H Cl H F H H H XXVIII-95 H NO₂ H F H H H XXVIII-96 H CN HF H H H XXVIII-97 H CONH₂ H F H H H XXVIII-98 H CONHMe H F H H HXXVIII-99 H CONMe₂ H F H H H XXVIII-100 H COMe H F H H H XXVIII-101 HCOOH H F H H H XXVIII-102 H COOMe H F H H H XXVIII-103 H CSOMe H F H H HXXVIII-104 H CSNH₂ H F H H H XXVIII-105 H CSNMe₂ H F H H H XXVIII-106 HCSNHMe H F H H H XXVIII-107 H OMe H F H H H XXVIII-108 H OEt H F H H HXXVIII-109 H OCOMe H F H H H XXVIII-110 H OCOOMe H F H H H XXVIII-111 HOCONHMe H F H H H XXVIII-112 H OCONMe₂ H F H H H XXVIII-113 H OCSMe H FH H H XXVIII-114 H OCSNMe₂ H F H H H XXVIII-115 H SMe H F H H HXXVIII-116 H SEt H F H H H XXVIII-117 H SCOMe H F H H H XXVIII-118 HSCSNMe₂ H F H H H XXVIII-119 H SCSNHMe H F H H H XXVIII-120 H NHMe H F HH H XXVIII-121 H NH₂ H F H H H XXVIII-122 H NMe₂ H F H H H XXVIII-123 HNHCOMe H F H H H XXVIII-124 H NHCONH₂ H F H H H XXVIII-125 H NHCONHMe HF H H H XXVIII-126 H NHCONMe₂ H F H H H XXVIII-127 H phenyl H F H H HXXVIII-128 H 2-chloro- H F H H H phenyl XXVIII-129 H 4-nitrophenyl H F HH H XXVIII-130 H 2-pyridyl H F H H H XXVIII-131 H 3-pyridyl H F H H HXXVIII-132 H 4-pyridyl H F H H H XXVIII-133 H 2-furyl H F H H HXXVIII-134 H PhO H F H H H XXVIII-135 CH₂ H F H H H XXVIII-136 H H H F HH H XXVIII-137 H Me H F H H H XXVIII-138 H Me F F H H H XXVIII-139 H EtH F H H H XXVIII-140 H Me Me F H H H XXVIII-141 Me H Me F H H HXXVIII-142 H F H F H H H XXVIII-143 Me F H F H H H XXVIII-144 Me H H MeH H H XXVIII-145 Et H H Me H H H XXVIII-146 vinyl H H Me H H HXXVIII-147 allyl H H Me H H H XXVIII-148 cyclopropyl H H Me H H HXXVIII-149 CN H H Me H H H XXVIII-150 CONH₂ H H Me H H H XXVIII-151CONHMe H H Me H H H XXVIII-152 CONMe₂ H H Me H H H XXVIII-153 COMe H HMe H H H XXVIII-154 COOH H H Me H H H XXVIII-155 COOMe H H Me H H HXXVIII-156 CSNHMe H H Me H H H XXVIII-157 H Me H Me H H H XXVIII-158 HEt H Me H H H XXVIII-159 H vinyl H Me H H H XXVIII-160 H allyl H Me H HH XXVIII-161 H cyclopropyl H Me H H H XXVIII-162 H F H Me H H HXXVIII-163 H Cl H Me H H H XXVIII-164 H NO₂ H Me H H H XXVIII-165 H CN HMe H H H XXVIII-166 H CONH₂ H Me H H H XXVIII-167 H CONHMe H Me H H HXXVIII-168 H CONMe₂ H Me H H H XXVIII-169 H COMe H Me H H H XXVIII-170 HCOOH H Me H H H XXVIII-171 H COOMe H Me H H H XXVIII-172 H CSOMe H Me HH H XXVIII-173 H CSNH₂ H Me H H H XXVIII-174 H CSNMe₂ H Me H H HXXVIII-175 H CSNHMe H Me H H H XXVIII-176 H OMe H Me H H H XXVIII-177 HOEt H Me H H H XXVIII-178 H OCOMe H Me H H H XXVIII-179 H OCOOMe H Me HH H XXVIII-180 H OCONHMe H Me H H H XXVIII-181 H OCONMe₂ H Me H H HXXVIII-182 H OCSMe H Me H H H XXVIII-183 H OCSNMe₂ H Me H H H XXVIII-184H SMe H Me H H H XXVIII-185 H SEt H Me H H H XXVIII-186 H SCOMe H Me H HH XXVIII-187 H SCSNMe₂ H Me H H H XXVIII-188 H SCSNHMe H Me H H HXXVIII-189 H NHMe H Me H H H XXVIII-190 H NH₂ H Me H H H XXVIII-191 HNMe₂ H Me H H H XXVIII-192 H NHCOMe H Me H H H XXVIII-193 H NHCONH₂ H MeH H H XXVIII-194 H NHCONHMe H Me H H H XXVIII-195 H NHCONMe₂ H Me H H HXXVIII-196 H phenyl H Me H H H XXVIII-197 H 2-chloro- H Me H H H phenylXXVIII-198 H 4-nitrophenyl H Me H H H XXVIII-199 H 2-pyridyl H Me H H HXXVIII-200 H 3-pyridyl H Me H H H XXVIII-201 H 4-pyridyl H Me H H HXXVIII-202 H 2-furyl H Me H H H XXVIII-203 H PhO H Me H H H XXVIII-204CH₂ H Me H H H XXVIII-205 H H H Me H H H XXVIII-206 H Me H Me H H HXXVIII-207 H Me F Me H H H XXVIII-208 H Et H Me H H H XXVIII-209 H Me MeMe H H H XXVIII-210 Me H Me Me H H H XXVIII-211 H F H Me H H HXXVIII-212 Me F H Me H H H XXVIII-213 Me H H F H F H XXVIII-214 Et H H FH F H XXVIII-215 vinyl H H F H F H XXVIII-216 allyl H H F H F HXXVIII-217 cyclopropyl H H F H F H XXVIII-218 CN H H F H F H XXVIII-219CONH₂ H H F H F H XXVIII-220 CONHMe H H F H F H XXVIII-221 CONMe₂ H H FH F H XXVIII-222 COMe H H F H F H XXVIII-223 COOH H H F H F H XXVIII-224COOMe H H F H F H XXVIII-225 CSNHMe H H F H F H XXVIII-226 H Me H F H FH XXVIII-227 H Et H F H F H XXVIII-228 H vinyl H F H F H XXVIII-229 Hallyl H F H F H XXVIII-230 H cyclopropyl H F H F H XXVIII-231 H F H F HF H XXVIII-232 H Cl H F H F H XXVIII-233 H NO₂ H F H F H XXVIII-234 H CNH F H F H XXVIII-235 H CONH₂ H F H F H XXVIII-236 H CONHMe H F H F HXXVIII-237 H CONMe₂ H F H F H XXVIII-238 H COMe H F H F H XXVIII-239 HCOOH H F H F H XXVIII-240 H COOMe H F H F H XXVIII-241 H CSOMe H F H F HXXVIII-242 H CSNH₂ H F H F H XXVIII-243 H CSNMe₂ H F H F H XXVIII-244 HCSNHMe H F H F H XXVIII-245 H OMe H F H F H XXVIII-246 H OEt H F H F HXXVIII-247 H OCOMe H F H F H XXVIII-248 H OCOOMe H F H F H XXVIII-249 HOCONHMe H F H F H XXVIII-250 H OCONMe₂ H F H F H XXVIII-251 H OCSMe H FH F H XXVIII-252 H OCSNMe₂ H F H F H XXVIII-253 H SMe H F H F HXXVIII-254 H SEt H F H F H XXVIII-255 H SCOMe H F H F H XXVIII-256 HSCSNMe₂ H F H F H XXVIII-257 H SCSNHMe H F H F H XXVIII-258 H NHMe H F HF H XXVIII-259 H NH₂ H F H F H XXVIII-260 H NMe₂ H F H F H XXVIII-261 HNHCOMe H F H F H XXVIII-262 H NHCONH₂ H F H F H XXVIII-263 H NHCONHMe HF H F H XXVIII-264 H NHCONMe₂ H F H F H XXVIII-265 H phenyl H F H F HXXVIII-266 H 2-chloro- H F H F H phenyl XXVIII-267 H 4-nitrophenyl H F HF H XXVIII-268 H 2-pyridyl H F H F H XXVIII-269 H 3-pyridyl H F H F HXXVIII-270 H 4-pyridyl H F H F H XXVIII-271 H 2-furyl H F H F HXXVIII-272 H PhO H F H F H XXVIII-273 CH₂ H F H F H XXVIII-274 H H H F HF H XXVIII-275 H Me H F H F H XXVIII-276 H Me F F H F H XXVIII-277 H EtH F H F H XXVIII-278 H Me Me F H F H XXVIII-279 Me H Me F H F HXXVIII-280 H F H F H F H XXVIII-281 Me F H F H F H XXVIII-282 H H H Me HH H XXVIII-283 H H H Et H H H XXVIII-284 H H H vinyl H H H XXVIII-285 HH H allyl H H H XXVIII-286 H H H cyclopropyl H H H XXVIII-287 H H H F HH H XXVIII-288 H H H Cl H H H XXVIII-289 H H H NO₂ H H H XXVIII-290 H HH CN H H H XXVIII-291 H H H CONH₂ H H H XXVIII-292 H H H CONHMe H H HXXVIII-293 H H H CONMe₂ H H H XXVIII-294 H H H COMe H H H XXVIII-295 H HH COOH H H H XXVIII-296 H H H COOMe H H H XXVIII-297 H H H CSOMe H H HXXVIII-298 H H H CSNH₂ H H H XXVIII-299 H H H CSNMe₂ H H H XXVIII-300 HH H CSNHMe H H H XXVIII-301 H H H OMe H H H XXVIII-302 H H H OEt H H HXXVIII-303 H H H OCOMe H H H XXVIII-304 H H H OCOOMe H H H XXVIII-305 HH H OCONHMe H H H XXVIII-306 H H H OCONMe₂ H H H XXVIII-307 H H H OCSMeH H H XXVIII-308 H H H OCSNMe₂ H H H XXVIII-309 H H H SMe H H HXXVIII-310 H H H SEt H H H XXVIII-311 H H H SCOMe H H H XXVIII-312 H H HSCSNMe₂ H H H XXVIII-313 H H H SCSNHMe H H H XXVIII-314 H H H NHMe H H HXXVIII-315 H H H NH₂ H H H XXVIII-316 H H H NMe₂ H H H XXVIII-317 H H HNHCOMe H H H XXVIII-318 H H H NHCONH₂ H H H XXVIII-319 H H H NHCONHMe HH H XXVIII-320 H H H NHCONMe₂ H H H XXVIII-321 H H H phenyl H H HXXVIII-322 H H H 2-chloro- H H H phenyl XXVIII-323 H H H 4-nitrophenyl HH H XXVIII-324 H H H 2-pyridyl H H H XXVIII-325 H H H 3-pyridyl H H HXXVIII-326 H H H 4-pyridyl H H H XXVIII-327 H H H 2-furyl H H HXXVIII-328 H H H PhO H H H XXVIII-329 H H H H H Me H XXVIII-330 H H H HH Et H XXVIII-331 H H H H H vinyl H XXVIII-332 H H H H H allyl HXXVIII-333 H H H H H cyclopropyl H XXVIII-334 H H H H H F H XXVIII-335 HH H H H Cl H XXVIII-336 H H H H H NO₂ H XXVIII-337 H H H H H CN HXXVIII-338 H H H H H CONH₂ H XXVIII-339 H H H H H CONHMe H XXVIII-340 HH H H H CONMe₂ H XXVIII-341 H H H H H COMe H XXVIII-342 H H H H H COOH HXXVIII-343 H H H H H COOMe H XXVIII-344 H H H H H CSOMe H XXVIII-345 H HH H H CSNH₂ H XXVIII-346 H H H H H CSNMe₂ H XXVIII-347 H H H H H CSNHMeH XXVIII-348 H H H H H OMe H XXVIII-349 H H H H H OEt H XXVIII-350 H H HH H OCOMe H XXVIII-351 H H H H H OCOOMe H XXVIII-352 H H H H H OCONHMe HXXVIII-353 H H H H H OCONMe₂ H XXVIII-354 H H H H H OCSMe H XXVIII-355 HH H H H OCSNMe₂ H XXVIII-356 H H H H H SMe H XXVIII-357 H H H H H SEt HXXVIII-358 H H H H H SCOMe H XXVIII-359 H H H H H SCSNMe₂ H XXVIII-360 HH H H H SCSNHMe H XXVIII-361 H H H H H NHMe H XXVIII-362 H H H H H NH₂ HXXVIII-363 H H H H H NMe₂ H XXVIII-364 H H H H H NHCOMe H XXVIII-365 H HH H H NHCONH₂ H XXVIII-366 H H H H H NHCONHMe H XXVIII-367 H H H H HNHCONMe₂ H XXVIII-368 H H H H H phenyl H XXVIII-369 H H H H H 2-chloro-H phenyl XXVIII-370 H H H H H 4-nitrophenyl H XXVIII-371 H H H H H2-pyridyl H XXVIII-372 H H H H H 3-pyridyl H XXVIII-373 H H H H H4-pyridyl H XXVIII-374 H H H H H 2-furyl H XXVIII-375 H H H H H PhO HXXVIII-376 H H H H H H Me XXVIII-377 H H H H H H Et XXVIII-378 H H H H HH Vinyl XXVIII-379 H H H H H H Allyl XXVIII-380 H H H H H H CyclopropylXXVIII-381 H H H H H H F XXVIII-382 H H H H H H Cl XXVIII-383 H H H H HH NO₂ XXVIII-384 H H H H H H CN XXVIII-385 H H H H H H CONH₂ XXVIII-386H H H H H H CONHMe XXVIII-387 H H H H H H CONMe₂ XXVIII-388 H H H H H HCOMe XXVIII-389 H H H H H H COOH XXVIII-390 H H H H H H COOMe XXVIII-391H H H H H H CSOMe XXVIII-392 H H H H H H CSNH₂ XXVIII-393 H H H H H HCSNMe₂ XXVIII-394 H H H H H H CSNHMe XXVIII-395 H H H H H H OMeXXVIII-396 H H H H H H OEt XXVIII-397 H H H H H H OCOMe XXVIII-398 H H HH H H OCOOMe XXVIII-399 H H H H H H OCONHMe XXVIII-400 H H H H H HOCONMe₂ XXVIII-401 H H H H H H OCSMe XXVIII-402 H H H H H H OCSNMe₂XXVIII-403 H H H H H H SMe XXVIII-404 H H H H H H SEt XXVIII-405 H H H HH H SCOMe XXVIII-406 H H H H H H SCSNMe₂ XXVIII-407 H H H H H H SCSNHMeXXVIII-408 H H H H H H NHMe XXVIII-409 H H H H H H NH₂ XXVIII-410 H H HH H H NMe₂ XXVIII-411 H H H H H H NHCOMe XXVIII-412 H H H H H H NHCONH₂XXVIII-413 H H H H H H NHCONHMe XXVIII-414 H H H H H H NHCONMe₂XXVIII-415 H H H H H H phenyl XXVIII-416 H H H H H H 2-chloro- phenylXXVIII-417 H H H H H H 4-nitrophenyl XXVIII-418 H H H H H H 2-pyridylXXVIII-419 H H H H H H 3-pyridyl XXVIII-420 H H H H H H 4-pyridylXXVIII-421 H H H H H H 2-furyl XXVIII-422 H H H H H H PhO

Table XXIX provides 422 compounds of formula Iac

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXX provides 422 compounds of formula Iad

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXI provides 422 compounds of formula Iae

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXII provides 422 compounds of formula Iaf

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXIII provides 422 compounds of formula Iag

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXIV provides 422 compounds of formula Iah

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXV provides 422 compounds of formula Iai

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXVI provides 4222 compounds of formula Iaj

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXVII provides 422 compounds of formula Iak

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d) and R⁹ aregiven in Table 4.

Table XXXVIII provides 391 compounds of formula Ial

wherein the values of Y, R¹, R², T^(a), T^(b), T^(c) and T^(d) are givenin Table 5.

TABLE 5 Compound No Y R1 R2 Ta Tb Tc Td XXXVIII-1 CH₂ H H N CH CH CHXXXVIII-2 CHMe H H N CH CH CH XXXVIII-3 CHEt H H N CH CH CH XXXVIII-4CHF H H N CH CH CH XXXVIII-5 C═CH₂ H H N CH CH CH XXXVIII-6 O H H N CHCH CH XXXVIII-7 S H H N CH CH CH XXXVIII-8 NH H H N CH CH CH XXXVIII-9NMe H H N CH CH CH XXXVIII-10 NCHO H H N CH CH CH XXXVIII-11 NCOMe H H NCH CH CH XXXVIII-12 CH₂ Me H N CH CH CH XXXVIII-13 O Me H N CH CH CHXXXVIII-14 CHMe Me H N CH CH CH XXXVIII-15 CH₂ ═O N CH CH CH XXXVIII-16CH₂ ═CH₂ N CH CH CH XXXVIII-17 CH₂ ═CHMe N CH CH CH XXXVIII-18 CH₂ H H NCH CF CH XXXVIII-19 CHMe H H N CH CF CH XXXVIII-20 CHEt H H N CH CF CHXXXVIII-21 CHF H H N CH CF CH XXXVIII-22 C═CH₂ H H N CH CF CH XXXVIII-23O H H N CH CF CH XXXVIII-24 S H H N CH CF CH XXXVIII-25 NH H H N CH CFCH XXXVIII-26 NMe H H N CH CF CH XXXVIII-27 NCHO H H N CH CF CHXXXVIII-28 NCOMe H H N CH CF CH XXXVIII-29 CH₂ Me H N CH CF CHXXXVIII-30 O Me H N CH CF CH XXXVIII-31 CHMe Me H N CH CF CH XXXVIII-32CH₂ ═O N CH CF CH XXXVIII-33 CH₂ ═CH₂ N CH CF CH XXXVIII-34 CH₂ ═CHMe NCH CF CH XXXVIII-35 CH₂ H H N CH CH CF XXXVIII-36 CHMe H H N CH CH CFXXXVIII-37 CHEt H H N CH CH CF XXXVIII-38 CHF H H N CH CH CF XXXVIII-39C═CH₂ H H N CH CH CF XXXVIII-40 O H H N CH CH CF XXXVIII-41 S H H N CHCH CF XXXVIII-42 NH H H N CH CH CF XXXVIII-43 NMe H H N CH CH CFXXXVIII-44 NCHO H H N CH CH CF XXXVIII-45 NCOMe H H N CH CH CFXXXVIII-46 CH₂ Me H N CH CH CF XXXVIII-47 O Me H N CH CH CF XXXVIII-48CHMe Me H N CH CH CF XXXVIII-49 CH₂ ═O N CH CH CF XXXVIII-50 CH₂ ═CH₂ NCH CH CF XXXVIII-51 CH₂ ═CHMe N CH CH CF XXXVIII-52 CH₂ H H CH N CH CHXXXVIII-53 CHMe H H CH N CH CH XXXVIII-54 CHEt H H CH N CH CH XXXVIII-55CHF H H CH N CH CH XXXVIII-56 C═CH₂ H H CH N CH CH XXXVIII-57 O H H CH NCH CH XXXVIII-58 S H H CH N CH CH XXXVIII-59 NH H H CH N CH CHXXXVIII-60 NMe H H CH N CH CH XXXVIII-61 NCHO H H CH N CH CH XXXVIII-62NCOMe H H CH N CH CH XXXVIII-63 CH₂ Me H CH N CH CH XXXVIII-64 O Me H CHN CH CH XXXVIII-65 CHMe Me H CH N CH CH XXXVIII-66 CH₂ ═O CH N CH CHXXXVIII-67 CH₂ ═CH₂ CH N CH CH XXXVIII-68 CH₂ ═CHMe CH N CH CHXXXVIII-69 CH₂ H H CF N CH CH XXXVIII-70 CHMe H H CF N CH CH XXXVIII-71CHEt H H CF N CH CH XXXVIII-72 CHF H H CF N CH CH XXXVIII-73 C═CH₂ H HCF N CH CH XXXVIII-74 O H H CF N CH CH XXXVIII-75 S H H CF N CH CHXXXVIII-76 NH H H CF N CH CH XXXVIII-77 NMe H H CF N CH CH XXXVIII-78NCHO H H CF N CH CH XXXVIII-79 NCOMe H H CF N CH CH XXXVIII-80 CH₂ Me HCF N CH CH XXXVIII-81 O Me H CF N CH CH XXXVIII-82 CHMe Me H CF N CH CHXXXVIII-83 CH₂ ═O CF N CH CH XXXVIII-84 CH₂ ═CH₂ CF N CH CH XXXVIII-85CH₂ ═CHMe CF N CH CH XXXVIII-86 CH₂ H H CMe N CH CH XXXVIII-87 CHMe H HCMe N CH CH XXXVIII-88 CHEt H H CMe N CH CH XXXVIII-89 CHF H H CMe N CHCH XXXVIII-90 C═CH₂ H H CMe N CH CH XXXVIII-91 O H H CMe N CH CHXXXVIII-92 S H H CMe N CH CH XXXVIII-93 NH H H CMe N CH CH XXXVIII-94NMe H H CMe N CH CH XXXVIII-95 NCHO H H CMe N CH CH XXXVIII-96 NCOMe H HCMe N CH CH XXXVIII-97 CH₂ Me H CMe N CH CH XXXVIII-98 O Me H CMe N CHCH XXXVIII-99 CHMe Me H CMe N CH CH XXXVIII-100 CH₂ ═O CMe N CH CHXXXVIII-101 CH₂ ═CH₂ CMe N CH CH XXXVIII-102 CH₂ ═CHMe CMe N CH CHXXXVIII-103 CH₂ H H CH N CF CH XXXVIII-104 CHMe H H CH N CF CHXXXVIII-105 CHEt H H CH N CF CH XXXVIII-106 CHF H H CH N CF CHXXXVIII-107 C═CH₂ H H CH N CF CH XXXVIII-108 O H H CH N CF CHXXXVIII-109 S H H CH N CF CH XXXVIII-110 NH H H CH N CF CH XXXVIII-111NMe H H CH N CF CH XXXVIII-112 NCHO H H CH N CF CH XXXVIII-113 NCOMe H HCH N CF CH XXXVIII-114 CH₂ Me H CH N CF CH XXXVIII-115 O Me H CH N CF CHXXXVIII-116 CHMe Me H CH N CF CH XXXVIII-117 CH₂ ═O CH N CF CHXXXVIII-118 CH₂ ═CH₂ CH N CF CH XXXVIII-119 CH₂ ═CHMe CH N CF CHXXXVIII-120 CH₂ H H CH N CH CF XXXVIII-121 CHMe H H CH N CH CFXXXVIII-122 CHEt H H CH N CH CF XXXVIII-123 CHF H H CH N CH CFXXXVIII-124 C═CH₂ H H CH N CH CF XXXVIII-125 O H H CH N CH CFXXXVIII-126 S H H CH N CH CF XXXVIII-127 NH H H CH N CH CF XXXVIII-128NMe H H CH N CH CF XXXVIII-129 NCHO H H CH N CH CF XXXVIII-130 NCOMe H HCH N CH CF XXXVIII-131 CH₂ Me H CH N CH CF XXXVIII-132 O Me H CH N CH CFXXXVIII-133 CHMe Me H CH N CH CF XXXVIII-134 CH₂ ═O CH N CH CFXXXVIII-135 CH₂ ═CH₂ CH N CH CF XXXVIII-136 CH₂ ═CHMe CH N CH CFXXXVIII-137 CH₂ H H CH CH N CH XXXVIII-138 CHMe H H CH CH N CHXXXVIII-139 CHEt H H CH CH N CH XXXVIII-140 CHF H H CH CH N CHXXXVIII-141 C═CH₂ H H CH CH N CH XXXVIII-142 O H H CH CH N CHXXXVIII-143 S H H CH CH N CH XXXVIII-144 NH H H CH CH N CH XXXVIII-145NMe H H CH CH N CH XXXVIII-146 NCHO H H CH CH N CH XXXVIII-147 NCOMe H HCH CH N CH XXXVIII-148 CH₂ Me H CH CH N CH XXXVIII-149 O Me H CH CH N CHXXXVIII-150 CHMe Me H CH CH N CH XXXVIII-151 CH₂ ═O CH CH N CHXXXVIII-152 CH₂ ═CH₂ CH CH N CH XXXVIII-153 CH₂ ═CHMe CH CH N CHXXXVIII-154 CH₂ H H CF CH N CH XXXVIII-155 CHMe H H CF CH N CHXXXVIII-156 CHEt H H CF CH N CH XXXVIII-157 CHF H H CF CH N CHXXXVIII-158 C═CH₂ H H CF CH N CH XXXVIII-159 O H H CF CH N CHXXXVIII-160 S H H CF CH N CH XXXVIII-161 NH H H CF CH N CH XXXVIII-162NMe H H CF CH N CH XXXVIII-163 NCHO H H CF CH N CH XXXVIII-164 NCOMe H HCF CH N CH XXXVIII-165 CH₂ Me H CF CH N CH XXXVIII-166 O Me H CF CH N CHXXXVIII-167 CHMe Me H CF CH N CH XXXVIII-168 CH₂ ═O CF CH N CHXXXVIII-169 CH₂ ═CH₂ CF CH N CH XXXVIII-170 CH₂ ═CHMe CF CH N CHXXXVIII-171 CH₂ H H CMe CH N CH XXXVIII-172 CHMe H H CMe CH N CHXXXVIII-173 CHEt H H CMe CH N CH XXXVIII-174 CHF H H CMe CH N CHXXXVIII-175 C═CH₂ H H CMe CH N CH XXXVIII-176 O H H CMe CH N CHXXXVIII-177 S H H CMe CH N CH XXXVIII-178 NH H H CMe CH N CH XXXVIII-179NMe H H CMe CH N CH XXXVIII-180 NCHO H H CMe CH N CH XXXVIII-181 NCOMe HH CMe CH N CH XXXVIII-182 CH₂ Me H CMe CH N CH XXXVIII-183 O Me H CMe CHN CH XXXVIII-184 CHMe Me H CMe CH N CH XXXVIII-185 CH₂ ═O CMe CH N CHXXXVIII-186 CH₂ ═CH₂ CMe CH N CH XXXVIII-187 CH₂ ═CHMe CMe CH N CHXXXVIII-188 CH₂ H H CH CH N CF XXXVIII-189 CHMe H H CH CH N CFXXXVIII-190 CHEt H H CH CH N CF XXXVIII-191 CHF H H CH CH N CFXXXVIII-192 C═CH₂ H H CH CH N CF XXXVIII-193 O H H CH CH N CFXXXVIII-194 S H H CH CH N CF XXXVIII-195 NH H H CH CH N CF XXXVIII-196NMe H H CH CH N CF XXXVIII-197 NCHO H H CH CH N CF XXXVIII-198 NCOMe H HCH CH N CF XXXVIII-199 CH₂ Me H CH CH N CF XXXVIII-200 O Me H CH CH N CFXXXVIII-201 CHMe Me H CH CH N CF XXXVIII-202 CH₂ ═O CH CH N CFXXXVIII-203 CH₂ ═CH₂ CH CH N CF XXXVIII-204 CH₂ ═CHMe CH CH N CFXXXVIII-205 CH₂ H H CH CH CH N XXXVIII-206 CHMe H H CH CH CH NXXXVIII-207 CHEt H H CH CH CH N XXXVIII-208 CHF H H CH CH CH NXXXVIII-209 C═CH₂ H H CH CH CH N XXXVIII-210 O H H CH CH CH NXXXVIII-211 S H H CH CH CH N XXXVIII-212 NH H H CH CH CH N XXXVIII-213NMe H H CH CH CH N XXXVIII-214 NCHO H H CH CH CH N XXXVIII-215 NCOMe H HCH CH CH N XXXVIII-216 CH₂ Me H CH CH CH N XXXVIII-217 O Me H CH CH CH NXXXVIII-218 CHMe Me H CH CH CH N XXXVIII-219 CH₂ ═O CH CH CH NXXXVIII-220 CH₂ ═CH₂ CH CH CH N XXXVIII-221 CH₂ ═CHMe CH CH CH NXXXVIII-222 CH₂ H H CF CH CH N XXXVIII-223 CHMe H H CF CH CH NXXXVIII-224 CHEt H H CF CH CH N XXXVIII-225 CHF H H CF CH CH NXXXVIII-226 C═CH₂ H H CF CH CH N XXXVIII-227 O H H CF CH CH NXXXVIII-228 S H H CF CH CH N XXXVIII-229 NH H H CF CH CH N XXXVIII-230NMe H H CF CH CH N XXXVIII-231 NCHO H H CF CH CH N XXXVIII-232 NCOMe H HCF CH CH N XXXVIII-233 CH₂ Me H CF CH CH N XXXVIII-234 O Me H CF CH CH NXXXVIII-235 CHMe Me H CF CH CH N XXXVIII-236 CH₂ ═O CF CH CH NXXXVIII-237 CH₂ ═CH₂ CF CH CH N XXXVIII-238 CH₂ ═CHMe CF CH CH NXXXVIII-239 CH₂ H H CMe CH CH N XXXVIII-240 CHMe H H CMe CH CH NXXXVIII-241 CHEt H H CMe CH CH N XXXVIII-242 CHF H H CMe CH CH NXXXVIII-243 C═CH₂ H H CMe CH CH N XXXVIII-244 O H H CMe CH CH NXXXVIII-245 S H H CMe CH CH N XXXVIII-246 NH H H CMe CH CH N XXXVIII-247NMe H H CMe CH CH N XXXVIII-248 NCHO H H CMe CH CH N XXXVIII-249 NCOMe HH CMe CH CH N XXXVIII-250 CH₂ Me H CMe CH CH N XXXVIII-251 O Me H CMe CHCH N XXXVIII-252 CHMe Me H CMe CH CH N XXXVIII-253 CH₂ ═O CMe CH CH NXXXVIII-254 CH₂ ═CH₂ CMe CH CH N XXXVIII-255 CH₂ ═CHMe CMe CH CH NXXXVIII-256 CH₂ H H CH CH CF N XXXVIII-257 CHMe H H CH CH CF NXXXVIII-258 CHEt H H CH CH CF N XXXVIII-259 CHF H H CH CH CF NXXXVIII-260 C═CH₂ H H CH CH CF N XXXVIII-261 O H H CH CH CF NXXXVIII-262 S H H CH CH CF N XXXVIII-263 NH H H CH CH CF N XXXVIII-264NMe H H CH CH CF N XXXVIII-265 NCHO H H CH CH CF N XXXVIII-266 NCOMe H HCH CH CF N XXXVIII-267 CH₂ Me H CH CH CF N XXXVIII-268 O Me H CH CH CF NXXXVIII-269 CHMe Me H CH CH CF N XXXVIII-270 CH₂ ═O CH CH CF NXXXVIII-271 CH₂ ═CH₂ CH CH CF N XXXVIII-272 CH₂ ═CHMe CH CH CF NXXXVIII-273 CH₂ H H N CH N CH XXXVIII-274 CHMe H H N CH N CH XXXVIII-275CHEt H H N CH N CH XXXVIII-276 CHF H H N CH N CH XXXVIII-277 C═CH₂ H H NCH N CH XXXVIII-278 O H H N CH N CH XXXVIII-279 S H H N CH N CHXXXVIII-280 NH H H N CH N CH XXXVIII-281 NMe H H N CH N CH XXXVIII-282NCHO H H N CH N CH XXXVIII-283 NCOMe H H N CH N CH XXXVIII-284 CH₂ Me HN CH N CH XXXVIII-285 O Me H N CH N CH XXXVIII-286 CHMe Me H N CH N CHXXXVIII-287 CH₂ ═O N CH N CH XXXVIII-288 CH₂ ═CH₂ N CH N CH XXXVIII-289CH₂ ═CHMe N CH N CH XXXVIII-290 CH₂ H H N CH N CF XXXVIII-291 CHMe H H NCH N CF XXXVIII-292 CHEt H H N CH N CF XXXVIII-293 CHF H H N CH N CFXXXVIII-294 C═CH₂ H H N CH N CF XXXVIII-295 O H H N CH N CF XXXVIII-296S H H N CH N CF XXXVIII-297 NH H H N CH N CF XXXVIII-298 NMe H H N CH NCF XXXVIII-299 NCHO H H N CH N CF XXXVIII-300 NCOMe H H N CH N CFXXXVIII-301 CH₂ Me H N CH N CF XXXVIII-302 O Me H N CH N CF XXXVIII-303CHMe Me H N CH N CF XXXVIII-304 CH₂ ═O N CH N CF XXXVIII-305 CH₂ ═CH₂ NCH N CF XXXVIII-306 CH₂ ═CHMe N CH N CF XXXVIII-307 CH₂ H H N N CH CHXXXVIII-308 CHMe H H N N CH CH XXXVIII-309 CHEt H H N N CH CHXXXVIII-310 CHF H H N N CH CH XXXVIII-311 C═CH₂ H H N N CH CHXXXVIII-312 O H H N N CH CH XXXVIII-313 S H H N N CH CH XXXVIII-314 NH HH N N CH CH XXXVIII-315 NMe H H N N CH CH XXXVIII-316 NCHO H H N N CH CHXXXVIII-317 NCOMe H H N N CH CH XXXVIII-318 CH₂ Me H N N CH CHXXXVIII-319 O Me H N N CH CH XXXVIII-320 CHMe Me H N N CH CH XXXVIII-321CH₂ ═O N N CH CH XXXVIII-322 CH₂ ═CH₂ N N CH CH XXXVIII-323 CH₂ ═CHMe NN CH CH XXXVIII-324 CH₂ H H N N CF CH XXXVIII-325 CHMe H H N N CF CHXXXVIII-326 CHEt H H N N CF CH XXXVIII-327 CHF H H N N CF CH XXXVIII-328C═CH₂ H H N N CF CH XXXVIII-329 O H H N N CF CH XXXVIII-330 S H H N N CFCH XXXVIII-331 NH H H N N CF CH XXXVIII-332 NMe H H N N CF CHXXXVIII-333 NCHO H H N N CF CH XXXVIII-334 NCOMe H H N N CF CHXXXVIII-335 CH₂ Me H N N CF CH XXXVIII-336 O Me H N N CF CH XXXVIII-337CHMe Me H N N CF CH XXXVIII-338 CH₂ ═O N N CF CH XXXVIII-339 CH₂ ═CH₂ NN CF CH XXXVIII-340 CH₂ ═CHMe N N CF CH XXXVIII-341 CH₂ H H N N CH CFXXXVIII-342 CHMe H H N N CH CF XXXVIII-343 CHEt H H N N CH CFXXXVIII-344 CHF H H N N CH CF XXXVIII-345 C═CH₂ H H N N CH CFXXXVIII-346 O H H N N CH CF XXXVIII-347 S H H N N CH CF XXXVIII-348 NH HH N N CH CF XXXVIII-349 NMe H H N N CH CF XXXVIII-350 NCHO H H N N CH CFXXXVIII-351 NCOMe H H N N CH CF XXXVIII-352 CH₂ Me H N N CH CFXXXVIII-353 O Me H N N CH CF XXXVIII-354 CHMe Me H N N CH CF XXXVIII-355CH₂ ═O N N CH CF XXXVIII-356 CH₂ ═CH₂ N N CH CF XXXVIII-357 CH₂ ═CHMe NN CH CF XXXVIII-358 CH₂ H H N CH CH N XXXVIII-359 CHMe H H N CH CH NXXXVIII-360 CHEt H H N CH CH N XXXVIII-361 CHF H H N CH CH N XXXVIII-362C═CH₂ H H N CH CH N XXXVIII-363 O H H N CH CH N XXXVIII-364 S H H N CHCH N XXXVIII-365 NH H H N CH CH N XXXVIII-366 NMe H H N CH CH NXXXVIII-367 NCHO H H N CH CH N XXXVIII-368 NCOMe H H N CH CH NXXXVIII-369 CH₂ Me H N CH CH N XXXVIII-370 O Me H N CH CH N XXXVIII-371CHMe Me H N CH CH N XXXVIII-372 CH₂ ═O N CH CH N XXXVIII-373 CH₂ ═CH₂ NCH CH N XXXVIII-374 CH₂ ═CHMe N CH CH N XXXVIII-375 CH₂ H H CH N CH NXXXVIII-376 CHMe H H CH N CH N XXXVIII-377 CHEt H H CH N CH NXXXVIII-378 CHF H H CH N CH N XXXVIII-379 C═CH₂ H H CH N CH NXXXVIII-380 O H H CH N CH N XXXVIII-381 S H H CH N CH N XXXVIII-382 NH HH CH N CH N XXXVIII-383 NMe H H CH N CH N XXXVIII-384 NCHO H H CH N CH NXXXVIII-385 NCOMe H H CH N CH N XXXVIII-386 CH₂ Me H CH N CH NXXXVIII-387 O Me H CH N CH N XXXVIII-388 CHMe Me H CH N CH N XXXVIII-389CH₂ ═O CH N CH N XXXVIII-390 CH₂ ═CH₂ CH N CH N XXXVIII-391 CH₂ ═CHMe CHN CH N

Table XXXIX provides 578 compounds of formula Iam

wherein the values of Y, R¹, R², T^(d), T^(e) and T^(f) are given inTable 6.

TABLE 6 Compound No Y R1 R2 Td Te Tf XXXIX-1 CH₂ H H NH CH CH XXXIX-2CHMe H H NH CH CH XXXIX-3 CHEt H H NH CH CH XXXIX-4 CHF H H NH CH CHXXXIX-5 C═CH₂ H H NH CH CH XXXIX-6 O H H NH CH CH XXXIX-7 S H H NH CH CHXXXIX-8 NH H H NH CH CH XXXIX-9 NMe H H NH CH CH XXXIX-10 NCHO H H NH CHCH XXXIX-11 NCOMe H H NH CH CH XXXIX-12 CH₂ Me H NH CH CH XXXIX-13 O MeH NH CH CH XXXIX-14 CHMe Me H NH CH CH XXXIX-15 CH₂ ═O NH CH CH XXXIX-16CH₂ ═CH₂ NH CH CH XXXIX-17 CH₂ ═CHMe NH CH CH XXXIX-18 CH₂ H H NH CF CHXXXIX-19 CHMe H H NH CF CH XXXIX-20 CHEt H H NH CF CH XXXIX-21 CHF H HNH CF CH XXXIX-22 C═CH₂ H H NH CF CH XXXIX-23 O H H NH CF CH XXXIX-24 SH H NH CF CH XXXIX-25 NH H H NH CF CH XXXIX-26 NMe H H NH CF CH XXXIX-27NCHO H H NH CF CH XXXIX-28 NCOMe H H NH CF CH XXXIX-29 CH₂ Me H NH CF CHXXXIX-30 O Me H NH CF CH XXXIX-31 CHMe Me H NH CF CH XXXIX-32 CH₂ ═O NHCF CH XXXIX-33 CH₂ ═CH₂ NH CF CH XXXIX-34 CH₂ ═CHMe NH CF CH XXXIX-35CH₂ H H NH CMe CH XXXIX-36 CHMe H H NH CMe CH XXXIX-37 CHEt H H NH CMeCH XXXIX-38 CHF H H NH CMe CH XXXIX-39 C═CH₂ H H NH CMe CH XXXIX-40 O HH NH CMe CH XXXIX-41 S H H NH CMe CH XXXIX-42 NH H H NH CMe CH XXXIX-43NMe H H NH CMe CH XXXIX-44 NCHO H H NH CMe CH XXXIX-45 NCOMe H H NH CMeCH XXXIX-46 CH₂ Me H NH CMe CH XXXIX-47 O Me H NH CMe CH XXXIX-48 CHMeMe H NH CMe CH XXXIX-49 CH₂ ═O NH CMe CH XXXIX-50 CH₂ ═CH₂ NH CMe CHXXXIX-51 CH₂ ═CHMe NH CMe CH XXXIX-52 CH₂ H H NH CH CMe XXXIX-53 CHMe HH NH CH CMe XXXIX-54 CHEt H H NH CH CMe XXXIX-55 CHF H H NH CH CMeXXXIX-56 C═CH₂ H H NH CH CMe XXXIX-57 O H H NH CH CMe XXXIX-58 S H H NHCH CMe XXXIX-59 NH H H NH CH CMe XXXIX-60 NMe H H NH CH CMe XXXIX-61NCHO H H NH CH CMe XXXIX-62 NCOMe H H NH CH CMe XXXIX-63 CH₂ Me H NH CHCMe XXXIX-64 O Me H NH CH CMe XXXIX-65 CHMe Me H NH CH CMe XXXIX-66 CH₂═O NH CH CMe XXXIX-67 CH₂ ═CH₂ NH CH CMe XXXIX-68 CH₂ ═CHMe NH CH CMeXXXIX-69 CH₂ H H NMe CH CH XXXIX-70 CHMe H H NMe CH CH XXXIX-71 CHEt H HNMe CH CH XXXIX-72 CHF H H NMe CH CH XXXIX-73 C═CH₂ H H NMe CH CHXXXIX-74 O H H NMe CH CH XXXIX-75 S H H NMe CH CH XXXIX-76 NH H H NMe CHCH XXXIX-77 NMe H H NMe CH CH XXXIX-78 NCHO H H NMe CH CH XXXIX-79 NCOMeH H NMe CH CH XXXIX-80 CH₂ Me H NMe CH CH XXXIX-81 O Me H NMe CH CHXXXIX-82 CHMe Me H NMe CH CH XXXIX-83 CH₂ ═O NMe CH CH XXXIX-84 CH₂ ═CH₂NMe CH CH XXXIX-85 CH₂ ═CHMe NMe CH CH XXXIX-86 CH₂ H H NMe CF CHXXXIX-87 CHMe H H NMe CF CH XXXIX-88 CHEt H H NMe CF CH XXXIX-89 CHF H HNMe CF CH XXXIX-90 C═CH₂ H H NMe CF CH XXXIX-91 O H H NMe CF CH XXXIX-92S H H NMe CF CH XXXIX-93 NH H H NMe CF CH XXXIX-94 NMe H H NMe CF CHXXXIX-95 NCHO H H NMe CF CH XXXIX-96 NCOMe H H NMe CF CH XXXIX-97 CH₂ MeH NMe CF CH XXXIX-98 O Me H NMe CF CH XXXIX-99 CHMe Me H NMe CF CHXXXIX-100 CH₂ ═O NMe CF CH XXXIX-101 CH₂ ═CH₂ NMe CF CH XXXIX-102 CH₂═CHMe NMe CF CH XXXIX-103 CH₂ H H NMe CMe CH XXXIX-104 CHMe H H NMe CMeCH XXXIX-105 CHEt H H NMe CMe CH XXXIX-106 CHF H H NMe CMe CH XXXIX-107C═CH₂ H H NMe CMe CH XXXIX-108 O H H NMe CMe CH XXXIX-109 S H H NMe CMeCH XXXIX-110 NH H H NMe CMe CH XXXIX-111 NMe H H NMe CMe CH XXXIX-112NCHO H H NMe CMe CH XXXIX-113 NCOMe H H NMe CMe CH XXXIX-114 CH₂ Me HNMe CMe CH XXXIX-115 O Me H NMe CMe CH XXXIX-116 CHMe Me H NMe CMe CHXXXIX-117 CH₂ ═O NMe CMe CH XXXIX-118 CH₂ ═CH₂ NMe CMe CH XXXIX-119 CH₂═CHMe NMe CMe CH XXXIX-120 CH₂ H H NMe CH CMe XXXIX-121 CHMe H H NMe CHCMe XXXIX-122 CHEt H H NMe CH CMe XXXIX-123 CHF H H NMe CH CMe XXXIX-124C═CH₂ H H NMe CH CMe XXXIX-125 O H H NMe CH CMe XXXIX-126 S H H NMe CHCMe XXXIX-127 NH H H NMe CH CMe XXXIX-128 NMe H H NMe CH CMe XXXIX-129NCHO H H NMe CH CMe XXXIX-130 NCOMe H H NMe CH CMe XXXIX-131 CH₂ Me HNMe CH CMe XXXIX-132 O Me H NMe CH CMe XXXIX-133 CHMe Me H NMe CH CMeXXXIX-134 CH₂ ═O NMe CH CMe XXXIX-135 CH₂ ═CH₂ NMe CH CMe XXXIX-136 CH₂═CHMe NMe CH CMe XXXIX-137 CH₂ H H O CH CH XXXIX-138 CHMe H H O CH CHXXXIX-139 CHEt H H O CH CH XXXIX-140 CHF H H O CH CH XXXIX-141 C═CH₂ H HO CH CH XXXIX-142 O H H O CH CH XXXIX-143 S H H O CH CH XXXIX-144 NH H HO CH CH XXXIX-145 NMe H H O CH CH XXXIX-146 NCHO H H O CH CH XXXIX-147NCOMe H H O CH CH XXXIX-148 CH₂ Me H O CH CH XXXIX-149 O Me H O CH CHXXXIX-150 CHMe Me H O CH CH XXXIX-151 CH₂ ═O O CH CH XXXIX-152 CH₂ ═CH₂O CH CH XXXIX-153 CH₂ ═CHMe O CH CH XXXIX-154 CH₂ H H O CF CH XXXIX-155CHMe H H O CF CH XXXIX-156 CHEt H H O CF CH XXXIX-157 CHF H H O CF CHXXXIX-158 C═CH₂ H H O CF CH XXXIX-159 O H H O CF CH XXXIX-160 S H H O CFCH XXXIX-161 NH H H O CF CH XXXIX-162 NMe H H O CF CH XXXIX-163 NCHO H HO CF CH XXXIX-164 NCOMe H H O CF CH XXXIX-165 CH₂ Me H O CF CH XXXIX-166O Me H O CF CH XXXIX-167 CHMe Me H O CF CH XXXIX-168 CH₂ ═O O CF CHXXXIX-169 CH₂ ═CH₂ O CF CH XXXIX-170 CH₂ ═CHMe O CF CH XXXIX-171 CH₂ H HO CMe CH XXXIX-172 CHMe H H O CMe CH XXXIX-173 CHEt H H O CMe CHXXXIX-174 CHF H H O CMe CH XXXIX-175 C═CH₂ H H O CMe CH XXXIX-176 O H HO CMe CH XXXIX-177 S H H O CMe CH XXXIX-178 NH H H O CMe CH XXXIX-179NMe H H O CMe CH XXXIX-180 NCHO H H O CMe CH XXXIX-181 NCOMe H H O CMeCH XXXIX-182 CH₂ Me H O CMe CH XXXIX-183 O Me H O CMe CH XXXIX-184 CHMeMe H O CMe CH XXXIX-185 CH₂ ═O O CMe CH XXXIX-186 CH₂ ═CH₂ O CMe CHXXXIX-187 CH₂ ═CHMe O CMe CH XXXIX-188 CH₂ H H O CH CMe XXXIX-189 CHMe HH O CH CMe XXXIX-190 CHEt H H O CH CMe XXXIX-191 CHF H H O CH CMeXXXIX-192 C═CH₂ H H O CH CMe XXXIX-193 O H H O CH CMe XXXIX-194 S H H OCH CMe XXXIX-195 NH H H O CH CMe XXXIX-196 NMe H H O CH CMe XXXIX-197NCHO H H O CH CMe XXXIX-198 NCOMe H H O CH CMe XXXIX-199 CH₂ Me H O CHCMe XXXIX-200 O Me H O CH CMe XXXIX-201 CHMe Me H O CH CMe XXXIX-202 CH₂═O O CH CMe XXXIX-203 CH₂ ═CH₂ O CH CMe XXXIX-204 CH₂ ═CHMe O CH CMeXXXIX-205 CH₂ H H S CH CH XXXIX-206 CHMe H H S CH CH XXXIX-207 CHEt H HS CH CH XXXIX-208 CHF H H S CH CH XXXIX-209 C═CH₂ H H S CH CH XXXIX-210O H H S CH CH XXXIX-211 S H H S CH CH XXXIX-212 NH H H S CH CH XXXIX-213NMe H H S CH CH XXXIX-214 NCHO H H S CH CH XXXIX-215 NCOMe H H S CH CHXXXIX-216 CH₂ Me H S CH CH XXXIX-217 O Me H S CH CH XXXIX-218 CHMe Me HS CH CH XXXIX-219 CH₂ ═O S CH CH XXXIX-220 CH₂ ═CH₂ S CH CH XXXIX-221CH₂ ═CHMe S CH CH XXXIX-222 CH₂ H H S CF CH XXXIX-223 CHMe H H S CF CHXXXIX-224 CHEt H H S CF CH XXXIX-225 CHF H H S CF CH XXXIX-226 C═CH₂ H HS CF CH XXXIX-227 O H H S CF CH XXXIX-228 S H H S CF CH XXXIX-229 NH H HS CF CH XXXIX-230 NMe H H S CF CH XXXIX-231 NCHO H H S CF CH XXXIX-232NCOMe H H S CF CH XXXIX-233 CH₂ Me H S CF CH XXXIX-234 O Me H S CF CHXXXIX-235 CHMe Me H S CF CH XXXIX-236 CH₂ ═O S CF CH XXXIX-237 CH₂ ═CH₂S CF CH XXXIX-238 CH₂ ═CHMe S CF CH XXXIX-239 CH₂ H H S CMe CH XXXIX-240CHMe H H S CMe CH XXXIX-241 CHEt H H S CMe CH XXXIX-242 CHF H H S CMe CHXXXIX-243 C═CH₂ H H S CMe CH XXXIX-244 O H H S CMe CH XXXIX-245 S H H SCMe CH XXXIX-246 NH H H S CMe CH XXXIX-247 NMe H H S CMe CH XXXIX-248NCHO H H S CMe CH XXXIX-249 NCOMe H H S CMe CH XXXIX-250 CH₂ Me H S CMeCH XXXIX-251 O Me H S CMe CH XXXIX-252 CHMe Me H S CMe CH XXXIX-253 CH₂═O S CMe CH XXXIX-254 CH₂ ═CH₂ S CMe CH XXXIX-255 CH₂ ═CHMe S CMe CHXXXIX-256 CH₂ H H S CH CMe XXXIX-257 CHMe H H S CH CMe XXXIX-258 CHEt HH S CH CMe XXXIX-259 CHF H H S CH CMe XXXIX-260 C═CH₂ H H S CH CMeXXXIX-261 O H H S CH CMe XXXIX-262 S H H S CH CMe XXXIX-263 NH H H S CHCMe XXXIX-264 NMe H H S CH CMe XXXIX-265 NCHO H H S CH CMe XXXIX-266NCOMe H H S CH CMe XXXIX-267 CH₂ Me H S CH CMe XXXIX-268 O Me H S CH CMeXXXIX-269 CHMe Me H S CH CMe XXXIX-270 CH₂ ═O S CH CMe XXXIX-271 CH₂═CH₂ S CH CMe XXXIX-272 CH₂ ═CHMe S CH CMe XXXIX-273 CH₂ H H NH N CHXXXIX-274 CHMe H H NH N CH XXXIX-275 CHEt H H NH N CH XXXIX-276 CHF H HNH N CH XXXIX-277 C═CH₂ H H NH N CH XXXIX-278 O H H NH N CH XXXIX-279 SH H NH N CH XXXIX-280 NH H H NH N CH XXXIX-281 NMe H H NH N CH XXXIX-282NCHO H H NH N CH XXXIX-283 NCOMe H H NH N CH XXXIX-284 CH₂ Me H NH N CHXXXIX-285 O Me H NH N CH XXXIX-286 CHMe Me H NH N CH XXXIX-287 CH₂ ═O NHN CH XXXIX-288 CH₂ ═CH₂ NH N CH XXXIX-289 CH₂ ═CHMe NH N CH XXXIX-290CH₂ H H NH N CMe XXXIX-291 CHMe H H NH N CMe XXXIX-292 CHEt H H NH N CMeXXXIX-293 CHF H H NH N CMe XXXIX-294 C═CH₂ H H NH N CMe XXXIX-295 O H HNH N CMe XXXIX-296 S H H NH N CMe XXXIX-297 NH H H NH N CMe XXXIX-298NMe H H NH N CMe XXXIX-299 NCHO H H NH N CMe XXXIX-300 NCOMe H H NH NCMe XXXIX-301 CH₂ Me H NH N CMe XXXIX-302 O Me H NH N CMe XXXIX-303 CHMeMe H NH N CMe XXXIX-304 CH₂ ═O NH N CMe XXXIX-305 CH₂ ═CH₂ NH N CMeXXXIX-306 CH₂ ═CHMe NH N CMe XXXIX-307 CH₂ H H NMe N CH XXXIX-308 CHMe HH NMe N CH XXXIX-309 CHEt H H NMe N CH XXXIX-310 CHF H H NMe N CHXXXIX-311 C═CH₂ H H NMe N CH XXXIX-312 O H H NMe N CH XXXIX-313 S H HNMe N CH XXXIX-314 NH H H NMe N CH XXXIX-315 NMe H H NMe N CH XXXIX-316NCHO H H NMe N CH XXXIX-317 NCOMe H H NMe N CH XXXIX-318 CH₂ Me H NMe NCH XXXIX-319 O Me H NMe N CH XXXIX-320 CHMe Me H NMe N CH XXXIX-321 CH₂═O NMe N CH XXXIX-322 CH₂ ═CH₂ NMe N CH XXXIX-323 CH₂ ═CHMe NMe N CHXXXIX-324 CH₂ H H NMe N CMe XXXIX-325 CHMe H H NMe N CMe XXXIX-326 CHEtH H NMe N CMe XXXIX-327 CHF H H NMe N CMe XXXIX-328 C═CH₂ H H NMe N CMeXXXIX-329 O H H NMe N CMe XXXIX-330 S H H NMe N CMe XXXIX-331 NH H H NMeN CMe XXXIX-332 NMe H H NMe N CMe XXXIX-333 NCHO H H NMe N CMe XXXIX-334NCOMe H H NMe N CMe XXXIX-335 CH₂ Me H NMe N CMe XXXIX-336 O Me H NMe NCMe XXXIX-337 CHMe Me H NMe N CMe XXXIX-338 CH₂ ═O NMe N CMe XXXIX-339CH₂ ═CH₂ NMe N CMe XXXIX-340 CH₂ ═CHMe NMe N CMe XXXIX-341 CH₂ H H O NCH XXXIX-342 CHMe H H O N CH XXXIX-343 CHEt H H O N CH XXXIX-344 CHF H HO N CH XXXIX-345 C═CH₂ H H O N CH XXXIX-346 O H H O N CH XXXIX-347 S H HO N CH XXXIX-348 NH H H O N CH XXXIX-349 NMe H H O N CH XXXIX-350 NCHO HH O N CH XXXIX-351 NCOMe H H O N CH XXXIX-352 CH₂ Me H O N CH XXXIX-353O Me H O N CH XXXIX-354 CHMe Me H O N CH XXXIX-355 CH₂ ═O O N CHXXXIX-356 CH₂ ═CH₂ O N CH XXXIX-357 CH₂ ═CHMe O N CH XXXIX-358 CH₂ H H ON CMe XXXIX-359 CHMe H H O N CMe XXXIX-360 CHEt H H O N CMe XXXIX-361CHF H H O N CMe XXXIX-362 C═CH₂ H H O N CMe XXXIX-363 O H H O N CMeXXXIX-364 S H H O N CMe XXXIX-365 NH H H O N CMe XXXIX-366 NMe H H O NCMe XXXIX-367 NCHO H H O N CMe XXXIX-368 NCOMe H H O N CMe XXXIX-369 CH₂Me H O N CMe XXXIX-370 O Me H O N CMe XXXIX-371 CHMe Me H O N CMeXXXIX-372 CH₂ ═O O N CMe XXXIX-373 CH₂ ═CH₂ O N CMe XXXIX-374 CH₂ ═CHMeO N CMe XXXIX-375 CH₂ H H S N CH XXXIX-376 CHMe H H S N CH XXXIX-377CHEt H H S N CH XXXIX-378 CHF H H S N CH XXXIX-379 C═CH₂ H H S N CHXXXIX-380 O H H S N CH XXXIX-381 S H H S N CH XXXIX-382 NH H H S N CHXXXIX-383 NMe H H S N CH XXXIX-384 NCHO H H S N CH XXXIX-385 NCOMe H H SN CH XXXIX-386 CH₂ Me H S N CH XXXIX-387 O Me H S N CH XXXIX-388 CHMe MeH S N CH XXXIX-389 CH₂ ═O S N CH XXXIX-390 CH₂ ═CH₂ S N CH XXXIX-391 CH₂═CHMe S N CH XXXIX-392 CH₂ H H S N CMe XXXIX-393 CHMe H H S N CMeXXXIX-394 CHEt H H S N CMe XXXIX-395 CHF H H S N CMe XXXIX-396 C═CH₂ H HS N CMe XXXIX-397 O H H S N CMe XXXIX-398 S H H S N CMe XXXIX-399 NH H HS N CMe XXXIX-400 NMe H H S N CMe XXXIX-401 NCHO H H S N CMe XXXIX-402NCOMe H H S N CMe XXXIX-403 CH₂ Me H S N CMe XXXIX-404 O Me H S N CMeXXXIX-405 CHMe Me H S N CMe XXXIX-406 CH₂ ═O S N CMe XXXIX-407 CH₂ ═CH₂S N CMe XXXIX-408 CH₂ ═CHMe S N CMe XXXIX-409 CH₂ H H NH CH N XXXIX-410CHMe H H NH CH N XXXIX-411 CHEt H H NH CH N XXXIX-412 CHF H H NH CH NXXXIX-413 C═CH₂ H H NH CH N XXXIX-414 O H H NH CH N XXXIX-415 S H H NHCH N XXXIX-416 NH H H NH CH N XXXIX-417 NMe H H NH CH N XXXIX-418 NCHO HH NH CH N XXXIX-419 NCOMe H H NH CH N XXXIX-420 CH₂ Me H NH CH NXXXIX-421 O Me H NH CH N XXXIX-422 CHMe Me H NH CH N XXXIX-423 CH₂ ═O NHCH N XXXIX-424 CH₂ ═CH₂ NH CH N XXXIX-425 CH₂ ═CHMe NH CH N XXXIX-426CH₂ H H NH CMe N XXXIX-427 CHMe H H NH CMe N XXXIX-428 CHEt H H NH CMe NXXXIX-429 CHF H H NH CMe N XXXIX-430 C═CH₂ H H NH CMe N XXXIX-431 O H HNH CMe N XXXIX-432 S H H NH CMe N XXXIX-433 NH H H NH CMe N XXXIX-434NMe H H NH CMe N XXXIX-435 NCHO H H NH CMe N XXXIX-436 NCOMe H H NH CMeN XXXIX-437 CH₂ Me H NH CMe N XXXIX-438 O Me H NH CMe N XXXIX-439 CHMeMe H NH CMe N XXXIX-440 CH₂ ═O NH CMe N XXXIX-441 CH₂ ═CH₂ NH CMe NXXXIX-442 CH₂ ═CHMe NH CMe N XXXIX-443 CH₂ H H O CH N XXXIX-444 CHMe H HO CH N XXXIX-445 CHEt H H O CH N XXXIX-446 CHF H H O CH N XXXIX-447C═CH₂ H H O CH N XXXIX-448 O H H O CH N XXXIX-449 S H H O CH N XXXIX-450NH H H O CH N XXXIX-451 NMe H H O CH N XXXIX-452 NCHO H H O CH NXXXIX-453 NCOMe H H O CH N XXXIX-454 CH₂ Me H O CH N XXXIX-455 O Me H OCH N XXXIX-456 CHMe Me H O CH N XXXIX-457 CH₂ ═O O CH N XXXIX-458 CH₂═CH₂ O CH N XXXIX-459 CH₂ ═CHMe O CH N XXXIX-460 CH₂ H H O CMe NXXXIX-461 CHMe H H O CMe N XXXIX-462 CHEt H H O CMe N XXXIX-463 CHF H HO CMe N XXXIX-464 C═CH₂ H H O CMe N XXXIX-465 O H H O CMe N XXXIX-466 SH H O CMe N XXXIX-467 NH H H O CMe N XXXIX-468 NMe H H O CMe N XXXIX-469NCHO H H O CMe N XXXIX-470 NCOMe H H O CMe N XXXIX-471 CH₂ Me H O CMe NXXXIX-472 O Me H O CMe N XXXIX-473 CHMe Me H O CMe N XXXIX-474 CH₂ ═O OCMe N XXXIX-475 CH₂ ═CH₂ O CMe N XXXIX-476 CH₂ ═CHMe O CMe N XXXIX-477CH₂ H H S CH N XXXIX-478 CHMe H H S CH N XXXIX-479 CHEt H H S CH NXXXIX-480 CHF H H S CH N XXXIX-481 C═CH₂ H H S CH N XXXIX-482 O H H S CHN XXXIX-483 S H H S CH N XXXIX-484 NH H H S CH N XXXIX-485 NMe H H S CHN XXXIX-486 NCHO H H S CH N XXXIX-487 NCOMe H H S CH N XXXIX-488 CH₂ MeH S CH N XXXIX-489 O Me H S CH N XXXIX-490 CHMe Me H S CH N XXXIX-491CH₂ ═O S CH N XXXIX-492 CH₂ ═CH₂ S CH N XXXIX-493 CH₂ ═CHMe S CH NXXXIX-494 CH₂ H H S CMe N XXXIX-495 CHMe H H S CMe N XXXIX-496 CHEt H HS CMe N XXXIX-497 CHF H H S CMe N XXXIX-498 C═CH₂ H H S CMe N XXXIX-499O H H S CMe N XXXIX-500 S H H S CMe N XXXIX-501 NH H H S CMe N XXXIX-502NMe H H S CMe N XXXIX-503 NCHO H H S CMe N XXXIX-504 NCOMe H H S CMe NXXXIX-505 CH₂ Me H S CMe N XXXIX-506 O Me H S CMe N XXXIX-507 CHMe Me HS CMe N XXXIX-508 CH₂ ═O S CMe N XXXIX-509 CH₂ ═CH₂ S CMe N XXXIX-510CH₂ ═CHMe S CMe N XXXIX-511 CH₂ H H NH N N XXXIX-512 CHMe H H NH N NXXXIX-513 CHEt H H NH N N XXXIX-514 CHF H H NH N N XXXIX-515 C═CH₂ H HNH N N XXXIX-516 O H H NH N N XXXIX-517 S H H NH N N XXXIX-518 NH H H NHN N XXXIX-519 NMe H H NH N N XXXIX-520 NCHO H H NH N N XXXIX-521 NCOMe HH NH N N XXXIX-522 CH₂ Me H NH N N XXXIX-523 O Me H NH N N XXXIX-524CHMe Me H NH N N XXXIX-525 CH₂ ═O NH N N XXXIX-526 CH₂ ═CH₂ NH N NXXXIX-527 CH₂ ═CHMe NH N N XXXIX-528 CH₂ H H NMe N N XXXIX-529 CHMe H HNMe N N XXXIX-530 CHEt H H NMe N N XXXIX-531 CHF H H NMe N N XXXIX-532C═CH₂ H H NMe N N XXXIX-533 O H H NMe N N XXXIX-534 S H H NMe N NXXXIX-535 NH H H NMe N N XXXIX-536 NMe H H NMe N N XXXIX-537 NCHO H HNMe N N XXXIX-538 NCOMe H H NMe N N XXXIX-539 CH₂ Me H NMe N N XXXIX-540O Me H NMe N N XXXIX-541 CHMe Me H NMe N N XXXIX-542 CH₂ ═O NMe N NXXXIX-543 CH₂ ═CH₂ NMe N N XXXIX-544 CH₂ ═CHMe NMe N N XXXIX-545 CH₂ H HO N N XXXIX-546 CHMe H H O N N XXXIX-547 CHEt H H O N N XXXIX-548 CHF HH O N N XXXIX-549 C═CH₂ H H O N N XXXIX-550 O H H O N N XXXIX-551 S H HO N N XXXIX-552 NH H H O N N XXXIX-553 NMe H H O N N XXXIX-554 NCHO H HO N N XXXIX-555 NCOMe H H O N N XXXIX-556 CH₂ Me H O N N XXXIX-557 O MeH O N N XXXIX-558 CHMe Me H O N N XXXIX-559 CH₂ ═O O N N XXXIX-560 CH₂═CH₂ O N N XXXIX-561 CH₂ ═CHMe O N N XXXIX-562 CH₂ H H S N N XXXIX-563CHMe H H S N N XXXIX-564 CHEt H H S N N XXXIX-565 CHF H H S N NXXXIX-566 C═CH₂ H H S N N XXXIX-567 O H H S N N XXXIX-568 S H H S N NXXXIX-569 NH H H S N N XXXIX-570 NMe H H S N N XXXIX-571 NCHO H H S N NXXXIX-572 NCOMe H H S N N XXXIX-573 CH₂ Me H S N N XXXIX-574 O Me H S NN XXXIX-575 CHMe Me H S N N XXXIX-576 CH₂ ═O S N N XXXIX-577 CH₂ ═CH₂ SN N XXXIX-578 CH₂ ═CHMe S N N

Table XL provides 392 compounds of formula Ian

wherein the values of Y, R¹, R₂, T^(d), T^(e) and T^(f) are given inTable 7.

TABLE 7 Compound No Y R1 R2 Td Te Tf XL-1 CH₂ H H CH NH CH XL-2 CHMe H HCH NH CH XL-3 CHEt H H CH NH CH XL-4 CHF H H CH NH CH XL-5 C═CH₂ H H CHNH CH XL-6 O H H CH NH CH XL-7 S H H CH NH CH XL-8 NH H H CH NH CH XL-9NMe H H CH NH CH XL-10 NCHO H H CH NH CH XL-11 NCOMe H H CH NH CH XL-12CH₂ Me H CH NH CH XL-13 O Me H CH NH CH XL-14 CHMe Me H CH NH CH XL-15CH₂ H H CMe NH CH XL-16 CHMe H H CMe NH CH XL-17 CHEt H H CMe NH CHXL-18 CHF H H CMe NH CH XL-19 C═CH₂ H H CMe NH CH XL-20 O H H CMe NH CHXL-21 S H H CMe NH CH XL-22 NH H H CMe NH CH XL-23 NMe H H CMe NH CHXL-24 NCHO H H CMe NH CH XL-25 NCOMe H H CMe NH CH XL-26 CH₂ Me H CMe NHCH XL-27 O Me H CMe NH CH XL-28 CHMe Me H CMe NH CH XL-29 CH₂ H H CH NHCMe XL-30 CHMe H H CH NH CMe XL-31 CHEt H H CH NH CMe XL-32 CHF H H CHNH CMe XL-33 C═CH₂ H H CH NH CMe XL-34 O H H CH NH CMe XL-35 S H H CH NHCMe XL-36 NH H H CH NH CMe XL-37 NMe H H CH NH CMe XL-38 NCHO H H CH NHCMe XL-39 NCOMe H H CH NH CMe XL-40 CH₂ Me H CH NH CMe XL-41 O Me H CHNH CMe XL-42 CHMe Me H CH NH CMe XL-43 CH₂ H H CMe NH CMe XL-44 CHMe H HCMe NH CMe XL-45 CHEt H H CMe NH CMe XL-46 CHF H H CMe NH CMe XL-47C═CH₂ H H CMe NH CMe XL-48 O H H CMe NH CMe XL-49 S H H CMe NH CMe XL-50NH H H CMe NH CMe XL-51 NMe H H CMe NH CMe XL-52 NCHO H H CMe NH CMeXL-53 NCOMe H H CMe NH CMe XL-54 CH₂ Me H CMe NH CMe XL-55 O Me H CMe NHCMe XL-56 CHMe Me H CMe NH CMe XL-57 CH₂ H H CH NMe CH XL-58 CHMe H H CHNMe CH XL-59 CHEt H H CH NMe CH XL-60 CHF H H CH NMe CH XL-61 C═CH₂ H HCH NMe CH XL-62 O H H CH NMe CH XL-63 S H H CH NMe CH XL-64 NH H H CHNMe CH XL-65 NMe H H CH NMe CH XL-66 NCHO H H CH NMe CH XL-67 NCOMe H HCH NMe CH XL-68 CH₂ Me H CH NMe CH XL-69 O Me H CH NMe CH XL-70 CHMe MeH CH NMe CH XL-71 CH₂ H H CMe NMe CH XL-72 CHMe H H CMe NMe CH XL-73CHEt H H CMe NMe CH XL-74 CHF H H CMe NMe CH XL-75 C═CH₂ H H CMe NMe CHXL-76 O H H CMe NMe CH XL-77 S H H CMe NMe CH XL-78 NH H H CMe NMe CHXL-79 NMe H H CMe NMe CH XL-80 NCHO H H CMe NMe CH XL-81 NCOMe H H CMeNMe CH XL-82 CH₂ Me H CMe NMe CH XL-83 O Me H CMe NMe CH XL-84 CHMe Me HCMe NMe CH XL-85 CH₂ H H CH NMe CMe XL-86 CHMe H H CH NMe CMe XL-87 CHEtH H CH NMe CMe XL-88 CHF H H CH NMe CMe XL-89 C═CH₂ H H CH NMe CMe XL-90O H H CH NMe CMe XL-91 S H H CH NMe CMe XL-92 NH H H CH NMe CMe XL-93NMe H H CH NMe CMe XL-94 NCHO H H CH NMe CMe XL-95 NCOMe H H CH NMe CMeXL-96 CH₂ Me H CH NMe CMe XL-97 O Me H CH NMe CMe XL-98 CHMe Me H CH NMeCMe XL-99 CH₂ H H CMe NMe CMe XL-100 CHMe H H CMe NMe CMe XL-101 CHEt HH CMe NMe CMe XL-102 CHF H H CMe NMe CMe XL-103 C═CH₂ H H CMe NMe CMeXL-104 O H H CMe NMe CMe XL-105 S H H CMe NMe CMe XL-106 NH H H CMe NMeCMe XL-107 NMe H H CMe NMe CMe XL-108 NCHO H H CMe NMe CMe XL-109 NCOMeH H CMe NMe CMe XL-110 CH₂ Me H CMe NMe CMe XL-111 O Me H CMe NMe CMeXL-112 CHMe Me H CMe NMe CMe XL-113 CH₂ H H CH O CH XL-114 CHMe H H CH OCH XL-115 CHEt H H CH O CH XL-116 CHF H H CH O CH XL-117 C═CH₂ H H CH OCH XL-118 O H H CH O CH XL-119 S H H CH O CH XL-120 NH H H CH O CHXL-121 NMe H H CH O CH XL-122 NCHO H H CH O CH XL-123 NCOMe H H CH O CHXL-124 CH₂ Me H CH O CH XL-125 O Me H CH O CH XL-126 CHMe Me H CH O CHXL-127 CH₂ H H CMe O CH XL-128 CHMe H H CMe O CH XL-129 CHEt H H CMe OCH XL-130 CHF H H CMe O CH XL-131 C═CH₂ H H CMe O CH XL-132 O H H CMe OCH XL-133 S H H CMe O CH XL-134 NH H H CMe O CH XL-135 NMe H H CMe O CHXL-136 NCHO H H CMe O CH XL-137 NCOMe H H CMe O CH XL-138 CH₂ Me H CMe OCH XL-139 O Me H CMe O CH XL-140 CHMe Me H CMe O CH XL-141 CH₂ H H CH OCMe XL-142 CHMe H H CH O CMe XL-143 CHEt H H CH O CMe XL-144 CHF H H CHO CMe XL-145 C═CH₂ H H CH O CMe XL-146 O H H CH O CMe XL-147 S H H CH OCMe XL-148 NH H H CH O CMe XL-149 NMe H H CH O CMe XL-150 NCHO H H CH OCMe XL-151 NCOMe H H CH O CMe XL-152 CH₂ Me H CH O CMe XL-153 O Me H CHO CMe XL-154 CHMe Me H CH O CMe XL-155 CH₂ H H CMe O CMe XL-156 CHMe H HCMe O CMe XL-157 CHEt H H CMe O CMe XL-158 CHF H H CMe O CMe XL-159C═CH₂ H H CMe O CMe XL-160 O H H CMe O CMe XL-161 S H H CMe O CMe XL-162NH H H CMe O CMe XL-163 NMe H H CMe O CMe XL-164 NCHO H H CMe O CMeXL-165 NCOMe H H CMe O CMe XL-166 CH₂ Me H CMe O CMe XL-167 O Me H CMe OCMe XL-168 CHMe Me H CMe O CMe XL-169 CH₂ H H CH S CH XL-170 CHMe H H CHS CH XL-171 CHEt H H CH S CH XL-172 CHF H H CH S CH XL-173 C═CH₂ H H CHS CH XL-174 O H H CH S CH XL-175 S H H CH S CH XL-176 NH H H CH S CHXL-177 NMe H H CH S CH XL-178 NCHO H H CH S CH XL-179 NCOMe H H CH S CHXL-180 CH₂ Me H CH S CH XL-181 O Me H CH S CH XL-182 CHMe Me H CH S CHXL-183 CH₂ H H CMe S CH XL-184 CHMe H H CMe S CH XL-185 CHEt H H CMe SCH XL-186 CHF H H CMe S CH XL-187 C═CH₂ H H CMe S CH XL-188 O H H CMe SCH XL-189 S H H CMe S CH XL-190 NH H H CMe S CH XL-191 NMe H H CMe S CHXL-192 NCHO H H CMe S CH XL-193 NCOMe H H CMe S CH XL-194 CH₂ Me H CMe SCH XL-195 O Me H CMe S CH XL-196 CHMe Me H CMe S CH XL-197 CH₂ H H CH SCMe XL-198 CHMe H H CH S CMe XL-199 CHEt H H CH S CMe XL-200 CHF H H CHS CMe XL-201 C═CH₂ H H CH S CMe XL-202 O H H CH S CMe XL-203 S H H CH SCMe XL-204 NH H H CH S CMe XL-205 NMe H H CH S CMe XL-206 NCHO H H CH SCMe XL-207 NCOMe H H CH S CMe XL-208 CH₂ Me H CH S CMe XL-209 O Me H CHS CMe XL-210 CHMe Me H CH S CMe XL-211 CH₂ H H CMe S CMe XL-212 CHMe H HCMe S CMe XL-213 CHEt H H CMe S CMe XL-214 CHF H H CMe S CMe XL-215C═CH₂ H H CMe S CMe XL-216 O H H CMe S CMe XL-217 S H H CMe S CMe XL-218NH H H CMe S CMe XL-219 NMe H H CMe S CMe XL-220 NCHO H H CMe S CMeXL-221 NCOMe H H CMe S CMe XL-222 CH₂ Me H CMe S CMe XL-223 O Me H CMe SCMe XL-224 CHMe Me H CMe S CMe XL-225 CH₂ H H N NMe CH XL-226 CHMe H H NNMe CH XL-227 CHEt H H N NMe CH XL-228 CHF H H N NMe CH XL-229 C═CH₂ H HN NMe CH XL-230 O H H N NMe CH XL-231 S H H N NMe CH XL-232 NH H H N NMeCH XL-233 NMe H H N NMe CH XL-234 NCHO H H N NMe CH XL-235 NCOMe H H NNMe CH XL-236 CH₂ Me H N NMe CH XL-237 O Me H N NMe CH XL-238 CHMe Me HN NMe CH XL-239 CH₂ H H N NMe CMe XL-240 CHMe H H N NMe CMe XL-241 CHEtH H N NMe CMe XL-242 CHF H H N NMe CMe XL-243 C═CH₂ H H N NMe CMe XL-244O H H N NMe CMe XL-245 S H H N NMe CMe XL-246 NH H H N NMe CMe XL-247NMe H H N NMe CMe XL-248 NCHO H H N NMe CMe XL-249 NCOMe H H N NMe CMeXL-250 CH₂ Me H N NMe CMe XL-251 O Me H N NMe CMe XL-252 CHMe Me H N NMeCMe XL-253 CH₂ H H N O CH XL-254 CHMe H H N O CH XL-255 CHEt H H N O CHXL-256 CHF H H N O CH XL-257 C═CH₂ H H N O CH XL-258 O H H N O CH XL-259S H H N O CH XL-260 NH H H N O CH XL-261 NMe H H N O CH XL-262 NCHO H HN O CH XL-263 NCOMe H H N O CH XL-264 CH₂ Me H N O CH XL-265 O Me H N OCH XL-266 CHMe Me H N O CH XL-267 CH₂ H H N O CMe XL-268 CHMe H H N OCMe XL-269 CHEt H H N O CMe XL-270 CHF H H N O CMe XL-271 C═CH₂ H H N OCMe XL-272 O H H N O CMe XL-273 S H H N O CMe XL-274 NH H H N O CMeXL-275 NMe H H N O CMe XL-276 NCHO H H N O CMe XL-277 NCOMe H H N O CMeXL-278 CH₂ Me H N O CMe XL-279 O Me H N O CMe XL-280 CHMe Me H N O CMeXL-281 CH₂ H H N S CH XL-282 CHMe H H N S CH XL-283 CHEt H H N S CHXL-284 CHF H H N S CH XL-285 C═CH₂ H H N S CH XL-286 O H H N S CH XL-287S H H N S CH XL-288 NH H H N S CH XL-289 NMe H H N S CH XL-290 NCHO H HN S CH XL-291 NCOMe H H N S CH XL-292 CH₂ Me H N S CH XL-293 O Me H N SCH XL-294 CHMe Me H N S CH XL-295 CH₂ H H N S CMe XL-296 CHMe H H N SCMe XL-297 CHEt H H N S CMe XL-298 CHF H H N S CMe XL-299 C═CH₂ H H N SCMe XL-300 O H H N S CMe XL-301 S H H N S CMe XL-302 NH H H N S CMeXL-303 NMe H H N S CMe XL-304 NCHO H H N S CMe XL-305 NCOMe H H N S CMeXL-306 CH₂ Me H N S CMe XL-307 O Me H N S CMe XL-308 CHMe Me H N S CMeXL-309 CH₂ H H CH NMe N XL-310 CHMe H H CH NMe N XL-311 CHEt H H CH NMeN XL-312 CHF H H CH NMe N XL-313 C═CH₂ H H CH NMe N XL-314 O H H CH NMeN XL-315 S H H CH NMe N XL-316 NH H H CH NMe N XL-317 NMe H H CH NMe NXL-318 NCHO H H CH NMe N XL-319 NCOMe H H CH NMe N XL-320 CH₂ Me H CHNMe N XL-321 O Me H CH NMe N XL-322 CHMe Me H CH NMe N XL-323 CH₂ H HCMe NMe N XL-324 CHMe H H CMe NMe N XL-325 CHEt H H CMe NMe N XL-326 CHFH H CMe NMe N XL-327 C═CH₂ H H CMe NMe N XL-328 O H H CMe NMe N XL-329 SH H CMe NMe N XL-330 NH H H CMe NMe N XL-331 NMe H H CMe NMe N XL-332NCHO H H CMe NMe N XL-333 NCOMe H H CMe NMe N XL-334 CH₂ Me H CMe NMe NXL-335 O Me H CMe NMe N XL-336 CHMe Me H CMe NMe N XL-337 CH₂ H H CH O NXL-338 CHMe H H CH O N XL-339 CHEt H H CH O N XL-340 CHF H H CH O NXL-341 C═CH₂ H H CH O N XL-342 O H H CH O N XL-343 S H H CH O N XL-344NH H H CH O N XL-345 NMe H H CH O N XL-346 NCHO H H CH O N XL-347 NCOMeH H CH O N XL-348 CH₂ Me H CH O N XL-349 O Me H CH O N XL-350 CHMe Me HCH O N XL-351 CH₂ H H CMe O N XL-352 CHMe H H CMe O N XL-353 CHEt H HCMe O N XL-354 CHF H H CMe O N XL-355 C═CH₂ H H CMe O N XL-356 O H H CMeO N XL-357 S H H CMe O N XL-358 NH H H CMe O N XL-359 NMe H H CMe O NXL-360 NCHO H H CMe O N XL-361 NCOMe H H CMe O N XL-362 CH₂ Me H CMe O NXL-363 O Me H CMe O N XL-364 CHMe Me H CMe O N XL-365 CH₂ H H CH S NXL-366 CHMe H H CH S N XL-367 CHEt H H CH S N XL-368 CHF H H CH S NXL-369 C═CH₂ H H CH S N XL-370 O H H CH S N XL-371 S H H CH S N XL-372NH H H CH S N XL-373 NMe H H CH S N XL-374 NCHO H H CH S N XL-375 NCOMeH H CH S N XL-376 CH₂ Me H CH S N XL-377 O Me H CH S N XL-378 CHMe Me HCH S N XL-379 CH₂ H H CMe S N XL-380 CHMe H H CMe S N XL-381 CHEt H HCMe S N XL-382 CHF H H CMe S N XL-383 C═CH₂ H H CMe S N XL-384 O H H CMeS N XL-385 S H H CMe S N XL-386 NH H H CMe S N XL-387 NMe H H CMe S NXL-388 NCHO H H CMe S N XL-389 NCOMe H H CMe S N XL-390 CH₂ Me H CMe S NXL-391 O Me H CMe S N XL-392 CHMe Me H CMe S N

Table XLI provides 336 compounds of formula Iao

wherein the values of Y, R¹, R², T^(d), T^(e) and T^(f) are given inTable 8.

TABLE 8 Compound No Y R1 R2 Td Te Tf XLI-1 CH₂ H H CH CH NH XLI-2 CHMe HH CH CH NH XLI-3 CHEt H H CH CH NH XLI-4 CHF H H CH CH NH XLI-5 C═CH₂ HH CH CH NH XLI-6 O H H CH CH NH XLI-7 S H H CH CH NH XLI-8 NH H H CH CHNH XLI-9 NMe H H CH CH NH XLI-10 NCHO H H CH CH NH XLI-11 NCOMe H H CHCH NH XLI-12 CH₂ Me H CH CH NH XLI-13 O Me H CH CH NH XLI-14 CHMe Me HCH CH NH XLI-15 CH₂ H H CMe CH NH XLI-16 CHMe H H CMe CH NH XLI-17 CHEtH H CMe CH NH XLI-18 CHF H H CMe CH NH XLI-19 C═CH₂ H H CMe CH NH XLI-20O H H CMe CH NH XLI-21 S H H CMe CH NH XLI-22 NH H H CMe CH NH XLI-23NMe H H CMe CH NH XLI-24 NCHO H H CMe CH NH XLI-25 NCOMe H H CMe CH NHXLI-26 CH₂ Me H CMe CH NH XLI-27 O Me H CMe CH NH XLI-28 CHMe Me H CMeCH NH XLI-29 CH₂ H H CH CMe NH XLI-30 CHMe H H CH CMe NH XLI-31 CHEt H HCH CMe NH XLI-32 CHF H H CH CMe NH XLI-33 C═CH₂ H H CH CMe NH XLI-34 O HH CH CMe NH XLI-35 S H H CH CMe NH XLI-36 NH H H CH CMe NH XLI-37 NMe HH CH CMe NH XLI-38 NCHO H H CH CMe NH XLI-39 NCOMe H H CH CMe NH XLI-40CH₂ Me H CH CMe NH XLI-41 O Me H CH CMe NH XLI-42 CHMe Me H CH CMe NHXLI-43 CH₂ H H CH CH NMe XLI-44 CHMe H H CH CH NMe XLI-45 CHEt H H CH CHNMe XLI-46 CHF H H CH CH NMe XLI-47 C═CH₂ H H CH CH NMe XLI-48 O H H CHCH NMe XLI-49 S H H CH CH NMe XLI-50 NH H H CH CH NMe XLI-51 NMe H H CHCH NMe XLI-52 NCHO H H CH CH NMe XLI-53 NCOMe H H CH CH NMe XLI-54 CH₂Me H CH CH NMe XLI-55 O Me H CH CH NMe XLI-56 CHMe Me H CH CH NMe XLI-57CH₂ H H CMe CH NMe XLI-58 CHMe H H CMe CH NMe XLI-59 CHEt H H CMe CH NMeXLI-60 CHF H H CMe CH NMe XLI-61 C═CH₂ H H CMe CH NMe XLI-62 O H H CMeCH NMe XLI-63 S H H CMe CH NMe XLI-64 NH H H CMe CH NMe XLI-65 NMe H HCMe CH NMe XLI-66 NCHO H H CMe CH NMe XLI-67 NCOMe H H CMe CH NMe XLI-68CH₂ Me H CMe CH NMe XLI-69 O Me H CMe CH NMe XLI-70 CHMe Me H CMe CH NMeXLI-71 CH₂ H H CH CMe NMe XLI-72 CHMe H H CH CMe NMe XLI-73 CHEt H H CHCMe NMe XLI-74 CHF H H CH CMe NMe XLI-75 C═CH₂ H H CH CMe NMe XLI-76 O HH CH CMe NMe XLI-77 S H H CH CMe NMe XLI-78 NH H H CH CMe NMe XLI-79 NMeH H CH CMe NMe XLI-80 NCHO H H CH CMe NMe XLI-81 NCOMe H H CH CMe NMeXLI-82 CH₂ Me H CH CMe NMe XLI-83 O Me H CH CMe NMe XLI-84 CHMe Me H CHCMe NMe XLI-85 CH₂ H H CH CH O XLI-86 CHMe H H CH CH O XLI-87 CHEt H HCH CH O XLI-88 CHF H H CH CH O XLI-89 C═CH₂ H H CH CH O XLI-90 O H H CHCH O XLI-91 S H H CH CH O XLI-92 NH H H CH CH O XLI-93 NMe H H CH CH OXLI-94 NCHO H H CH CH O XLI-95 NCOMe H H CH CH O XLI-96 CH₂ Me H CH CH OXLI-97 O Me H CH CH O XLI-98 CHMe Me H CH CH O XLI-99 CH₂ H H CMe CH OXLI-100 CHMe H H CMe CH O XLI-101 CHEt H H CMe CH O XLI-102 CHF H H CMeCH O XLI-103 C═CH₂ H H CMe CH O XLI-104 O H H CMe CH O XLI-105 S H H CMeCH O XLI-106 NH H H CMe CH O XLI-107 NMe H H CMe CH O XLI-108 NCHO H HCMe CH O XLI-109 NCOMe H H CMe CH O XLI-110 CH₂ Me H CMe CH O XLI-111 OMe H CMe CH O XLI-112 CHMe Me H CMe CH O XLI-113 CH₂ H H CH CMe OXLI-114 CHMe H H CH CMe O XLI-115 CHEt H H CH CMe O XLI-116 CHF H H CHCMe O XLI-117 C═CH₂ H H CH CMe O XLI-118 O H H CH CMe O XLI-119 S H H CHCMe O XLI-120 NH H H CH CMe O XLI-121 NMe H H CH CMe O XLI-122 NCHO H HCH CMe O XLI-123 NCOMe H H CH CMe O XLI-124 CH₂ Me H CH CMe O XLI-125 OMe H CH CMe O XLI-126 CHMe Me H CH CMe O XLI-127 CH₂ H H CH CH S XLI-128CHMe H H CH CH S XLI-129 CHEt H H CH CH S XLI-130 CHF H H CH CH SXLI-131 C═CH₂ H H CH CH S XLI-132 O H H CH CH S XLI-133 S H H CH CH SXLI-134 NH H H CH CH S XLI-135 NMe H H CH CH S XLI-136 NCHO H H CH CH SXLI-137 NCOMe H H CH CH S XLI-138 CH₂ Me H CH CH S XLI-139 O Me H CH CHS XLI-140 CHMe Me H CH CH S XLI-141 CH₂ H H CMe CH S XLI-142 CHMe H HCMe CH S XLI-143 CHEt H H CMe CH S XLI-144 CHF H H CMe CH S XLI-145C═CH₂ H H CMe CH S XLI-146 O H H CMe CH S XLI-147 S H H CMe CH S XLI-148NH H H CMe CH S XLI-149 NMe H H CMe CH S XLI-150 NCHO H H CMe CH SXLI-151 NCOMe H H CMe CH S XLI-152 CH₂ Me H CMe CH S XLI-153 O Me H CMeCH S XLI-154 CHMe Me H CMe CH S XLI-155 CH₂ H H CH CMe S XLI-156 CHMe HH CH CMe S XLI-157 CHEt H H CH CMe S XLI-158 CHF H H CH CMe S XLI-159C═CH₂ H H CH CMe S XLI-160 O H H CH CMe S XLI-161 S H H CH CMe S XLI-162NH H H CH CMe S XLI-163 NMe H H CH CMe S XLI-164 NCHO H H CH CMe SXLI-165 NCOMe H H CH CMe S XLI-166 CH₂ Me H CH CMe S XLI-167 O Me H CHCMe S XLI-168 CHMe Me H CH CMe S XLI-169 CH₂ H H N CH NMe XLI-170 CHMe HH N CH NMe XLI-171 CHEt H H N CH NMe XLI-172 CHF H H N CH NMe XLI-173C═CH₂ H H N CH NMe XLI-174 O H H N CH NMe XLI-175 S H H N CH NMe XLI-176NH H H N CH NMe XLI-177 NMe H H N CH NMe XLI-178 NCHO H H N CH NMeXLI-179 NCOMe H H N CH NMe XLI-180 CH₂ Me H N CH NMe XLI-181 O Me H N CHNMe XLI-182 CHMe Me H N CH NMe XLI-183 CH₂ H H N CMe NMe XLI-184 CHMe HH N CMe NMe XLI-185 CHEt H H N CMe NMe XLI-186 CHF H H N CMe NMe XLI-187C═CH₂ H H N CMe NMe XLI-188 O H H N CMe NMe XLI-189 S H H N CMe NMeXLI-190 NH H H N CMe NMe XLI-191 NMe H H N CMe NMe XLI-192 NCHO H H NCMe NMe XLI-193 NCOMe H H N CMe NMe XLI-194 CH₂ Me H N CMe NMe XLI-195 OMe H N CMe NMe XLI-196 CHMe Me H N CMe NMe XLI-197 CH₂ H H N CH OXLI-198 CHMe H H N CH O XLI-199 CHEt H H N CH O XLI-200 CHF H H N CH OXLI-201 C═CH₂ H H N CH O XLI-202 O H H N CH O XLI-203 S H H N CH OXLI-204 NH H H N CH O XLI-205 NMe H H N CH O XLI-206 NCHO H H N CH OXLI-207 NCOMe H H N CH O XLI-208 CH₂ Me H N CH O XLI-209 O Me H N CH OXLI-210 CHMe Me H N CH O XLI-211 CH₂ H H N CMe O XLI-212 CHMe H H N CMeO XLI-213 CHEt H H N CMe O XLI-214 CHF H H N CMe O XLI-215 C═CH₂ H H NCMe O XLI-216 O H H N CMe O XLI-217 S H H N CMe O XLI-218 NH H H N CMe OXLI-219 NMe H H N CMe O XLI-220 NCHO H H N CMe O XLI-221 NCOMe H H N CMeO XLI-222 CH₂ Me H N CMe O XLI-223 O Me H N CMe O XLI-224 CHMe Me H NCMe O XLI-225 CH₂ H H N CH S XLI-226 CHMe H H N CH S XLI-227 CHEt H H NCH S XLI-228 CHF H H N CH S XLI-229 C═CH₂ H H N CH S XLI-230 O H H N CHS XLI-231 S H H N CH S XLI-232 NH H H N CH S XLI-233 NMe H H N CH SXLI-234 NCHO H H N CH S XLI-235 NCOMe H H N CH S XLI-236 CH₂ Me H N CH SXLI-237 O Me H N CH S XLI-238 CHMe Me H N CH S XLI-239 CH₂ H H N CMe SXLI-240 CHMe H H N CMe S XLI-241 CHEt H H N CMe S XLI-242 CHF H H N CMeS XLI-243 C═CH₂ H H N CMe S XLI-244 O H H N CMe S XLI-245 S H H N CMe SXLI-246 NH H H N CMe S XLI-247 NMe H H N CMe S XLI-248 NCHO H H N CMe SXLI-249 NCOMe H H N CMe S XLI-250 CH₂ Me H N CMe S XLI-251 O Me H N CMeS XLI-252 CHMe Me H N CMe S XLI-253 CH₂ H H CH N NMe XLI-254 CHMe H H CHN NMe XLI-255 CHEt H H CH N NMe XLI-256 CHF H H CH N NMe XLI-257 C═CH₂ HH CH N NMe XLI-258 O H H CH N NMe XLI-259 S H H CH N NMe XLI-260 NH H HCH N NMe XLI-261 NMe H H CH N NMe XLI-262 NCHO H H CH N NMe XLI-263NCOMe H H CH N NMe XLI-264 CH₂ Me H CH N NMe XLI-265 O Me H CH N NMeXLI-266 CHMe Me H CH N NMe XLI-267 CH₂ H H CMe N NMe XLI-268 CHMe H HCMe N NMe XLI-269 CHEt H H CMe N NMe XLI-270 CHF H H CMe N NMe XLI-271C═CH₂ H H CMe N NMe XLI-272 O H H CMe N NMe XLI-273 S H H CMe N NMeXLI-274 NH H H CMe N NMe XLI-275 NMe H H CMe N NMe XLI-276 NCHO H H CMeN NMe XLI-277 NCOMe H H CMe N NMe XLI-278 CH₂ Me H CMe N NMe XLI-279 OMe H CMe N NMe XLI-280 CHMe Me H CMe N NMe XLI-281 CH₂ H H CH N OXLI-282 CHMe H H CH N O XLI-283 CHEt H H CH N O XLI-284 CHF H H CH N OXLI-285 C═CH₂ H H CH N O XLI-286 O H H CH N O XLI-287 S H H CH N OXLI-288 NH H H CH N O XLI-289 NMe H H CH N O XLI-290 NCHO H H CH N OXLI-291 NCOMe H H CH N O XLI-292 CH₂ Me H CH N O XLI-293 O Me H CH N OXLI-294 CHMe Me H CH N O XLI-295 CH₂ H H CMe N O XLI-296 CHMe H H CMe NO XLI-297 CHEt H H CMe N O XLI-298 CHF H H CMe N O XLI-299 C═CH₂ H H CMeN O XLI-300 O H H CMe N O XLI-301 S H H CMe N O XLI-302 NH H H CMe N OXLI-303 NMe H H CMe N O XLI-304 NCHO H H CMe N O XLI-305 NCOMe H H CMe NO XLI-306 CH₂ Me H CMe N O XLI-307 O Me H CMe N O XLI-308 CHMe Me H CMeN O XLI-309 CH₂ H H CH N S XLI-310 CHMe H H CH N S XLI-311 CHEt H H CH NS XLI-312 CHF H H CH N S XLI-313 C═CH₂ H H CH N S XLI-314 O H H CH N SXLI-315 S H H CH N S XLI-316 NH H H CH N S XLI-317 NMe H H CH N SXLI-318 NCHO H H CH N S XLI-319 NCOMe H H CH N S XLI-320 CH₂ Me H CH N SXLI-321 O Me H CH N S XLI-322 CHMe Me H CH N S XLI-323 CH₂ H H CMe N SXLI-324 CHMe H H CMe N S XLI-325 CHEt H H CMe N S XLI-326 CHF H H CMe NS XLI-327 C═CH₂ H H CMe N S XLI-328 O H H CMe N S XLI-329 S H H CMe N SXLI-330 NH H H CMe N S XLI-331 NMe H H CMe N S XLI-332 NCHO H H CMe N SXLI-333 NCOMe H H CMe N S XLI-334 CH₂ Me H CMe N S XLI-335 O Me H CMe NS XLI-336 CHMe Me H CMe N S

Table XLII provides 612 compounds of formula Iap

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andR⁹ are given in Table 3.

Table XLIII provides 612 compounds of formula Iaq

wherein the values of R¹, R², R^(4a), R^(4b), R^(4c), R^(4d), R⁵, R⁶ andgiven in Table 3.

The following tables provide characterising data for some of thecompounds in Tables I-XLIII; other compounds are only described in thesetables.

TABLE 1 Characterising Data

Cpd.No R1 Y R4a R4b R4c R4d Mp [° C.] 1.001 H CH₂ F H H F Solid 1.002 HCH₂ H H Br H 167-169 1.003 H CH₂ H H Cl H 164-166 1.004 H CH₂ H H Me H156-157 1.005 H CH₂ F H F H 175-178 1.006 H CH₂ MeO H H MeO 163-1651.007 H CH₂ Me H Me H 153-155 1.008 H CH₂ H H MeO H 159-161 1.009 H CH₂H MeO H H 148-150 1.010 H CH₂ MeO H H H 178-179 1.011 H CH₂ H Me MeO H141-143 1.012 H CHMe H H H H 112-115 1.013 Me CH₂ H H H H 166-168 1.014H S H Me H H 234-235 1.015 H O H Me H H 133-134 1.016 H CH₂ OH H H HDecomp. 100 1.017 H CH₂ OCH2OMe H H H 171 1.018 H CH₂ H H H H 160 1.019H O Cl H H H 185 1.020^(a)) Me CH₂ H H H H resin 1.021 H S H H H H resinR2, R7, R8, R9 = H ^(a))R2 = Me

TABLE 2 Characterising Data

Cpd.No R1 R2 R5 R6 R4a R4b R4c R4d Mp [° C.] 2.001^(a)) H H H H H H H HSolid 2.002 H H H H H H H H 137 2.003^(b)) H H H H H H H H 1232.004^(c)) H H H H H H H H 123 2.005 H H H H H F H H 136 2.006 H H H HMe H H H 134 2.007 H H H H H H Me H 181 2.008 H H H H Br H H Me Solid2.009 H H H H Me H H Br Solid 2.010 H H H H H H H OCH₂OMe Oil 2.011 H HH H OCH₂OMe H H H Solid 2.012 H H H H OH H H H 191 2.013 H H H H OTf H HH Resin 2.014 H H H H Et H H H Solid 2.015 H H H H OH H H H 125 Decomp.2.016 H H H H H H H Me 117-120 2.017 H H H H H OCH₂OMe H H 150-153 2.018H H H H OMe H H H Solid 2.019 H H H H F H H H 149 2.020 H H H H Cl H H H124-127 2.021^(c)) H H H H Me H H H 119 2.022^(b)) H H H H Me H H H 1222.023 H H H H F F H H 161 2.024 H H H H F H F H 145-152 2.025 H H H H FH H F 182 2.026 H H H H F H Br H 156 2.027 H H Me Me H H H H  60-662.028 H H H H F F F H 123 2.029 H H H H H OH H H 75 Decomp. 2.030 H H HH F H F F 172 2.031 H H H H F H Me H 184 2.032^(d)) Me H H H H H H HSolid 2.033 Me Me H H H H H H 119 2.034 Pr Pr H H H H H H 101-103 2.035H H H H H Me OMe H 152-153 2.036 H H H H F F F F 165 2.037 H H H H F HPh H Solid 2.038 H H H H F H Et H 148-149 2.039 H H H H COOMe H H H 1312.040^(e)) H CH₂ H H H H H 173-175 2.041 H H H H PhO H H H 143-146 2.042H H H H NO₂ H H H 144-145 2.043 H H H H (mCF₃)PhO H H H 115-116 2.044 HH H H CN H H H Resin 2.045 H H H H pClPhO H H H 163-164 2.046 H H H H IH H H 170-171 2.047 H H H H Me₃SiC≡C H H H Solid 2.048 H H H H HC≡C H HH Oil 2.048 H H OBn H F H F H Cis Oil 2.049 H H H H H H Br H solid 2.050H H H H H H H Cl solid 2.051 H H H H H H H NHAc solid 2.052 H H H H H HH F 171-172 2.053 H H H H m-CF₃-phenyl H H H 103-105 2.054 H H H H PhCC—H H H 160-161 2.055 H H H H p-Cl-phenyl H H H 187-188 2.056 H H H Hvinyl H H H solid 2.057 H H H H formyl H H H 142-143 2.058 H H H H CHF₂H H H 116-117 2.059 H H H H MeOCH═N— H H H resin 2.060 H H N₃ H F H F HCis Resin 2.061 H H SMe H F H F H Cis Resin 2.062 H H H H CCl₃ H H HSolid 2.063 H H NH₂ H F H F H Trans Resin 2.064 ═CH₂ H H H H H H 107-1112.066 H —CH₂— H H H H H Exo124-129 2.067 F H H H F H H H Trans 142-1442.068 H H SMe H SMe H F H Trans 143-149 2.069 F H S(O)Me H F H H H Cissolid 2.070 H H COOMe H H H H H Cis 105-107 ^(a))HCl salt ^(b))S-isomer^(c))R-isomer ^(d))mixture of cis and trans ^(e))endo

TABLE 3 Characterising Data

Mp Cpd.No. Y CR9-CR1R2 R4a R4b R4c R4d [° C.] 3.002 0 CH—CF2 Me H H H162 3.004 CH₂ CMe—CH2 H H H H a) a)¹H-NMR (300 MHz CDCl₃) 1.68 (3H, s,Me); 2.18 (1H, m); 2.73 (1H, m); 2.88 (1H, m); 3.03 (1H, m); 3.22 (2H,t); 3.98 (2H, m); 7.27 (4H, m).

TABLE 4 Characterising Data

Cpd.No. Td Te Tf R7 R8 Mp 4.001 S CH CH H H 147-149 4.002 NMe CH H H H154-156 4.003 O N CMe H H 141-143 4.004 O CMe CH H H 148-150 4.005 O CMeCH Me Me  87-89 4.006 O CH CH Me Me resin

Characterising Data-5

Cpd. Phys. No. Ta Tb Tc Td Y R10 Data 5.001 N CMe N CH CH₂CH₂ H Oil5.002 N C—CF₃ CH CH CH₂ H solid 5.003 N C—CHF₂ CH CH CH₂CH₂ H solid5.004 N C—CF₃ CH CH CH₂CMe₂ H  74-75 5.005 N CH CH CH CH₂ H solid 5.006N C—CF₃ CH CH CH₂ CN solid 5.007 N C—CF₃ CH CH CH₂ Boc 144-147

TABLE 6 Characterising Data

Cpd.No. R1 R2 Y R4a R4b R4c R4d Isomer Mp [° C.] 6.001 H H C═O H H H H145-147 6.002 F F CHF H H H H a) 6.003 H H CH₂ H H H Et  98-100 6.004 HH CHOH F H F H cis 167 6.005 H H SO₂ H H H H 164-166 6.006 H H CH₂ H BrH H 137-139 6.007 H H CH₂ OCHF₂ H H H Oil 6.008 H H CH₂ OCSNMe₂ H H HResin 6.009 Me H CH₂ H H H H trans 122 6.010 H H CHOH H H H H trans 1496.011 H H CH₂ H H H nPr  72-75 6.012 Me H CH₂ H H H H cis Solid 6.013iPr H CH₂ H H H H cis Solid 6.014 H H CH₂ COOBu H H H Resin 6.015 Et HCH₂ H H H H cis Solid 6.016 Et H CH₂ H H H H trans Solid 6.017 H H CHEtH H H H 1:5 c:t brown solid 6.018 H H CHiPr H H H H 1:1 c:t oil 6.019 HH CHMe H H H H cis 126 6.020 H H CHMe H H H H 1:3 c:t 139 6.021 H H C═OF H F H 144-155 6.022 F H H F H H H cis 159 6.023 H H CHF F H F H transbrown crystals 6.024 H H CHF F H F H cis brown crystals 6.025 COOBu HCH₂ H H H H trans  99-109 6.026 COOMe H CH₂ H H H H trans yellow oil6.027 CH₂OH H CH₂ H H H H cis 147-148 6.028 COONa H CH₂ H H H H cis >2006.029 CONHBn H CH₂ H H H H cis 194-198 6.030 H H CHOMe F H F H cis115-116 6.031 H H O H H H H 135-156 6.032 OH H CH₂ H H H H trans 182-2026.033 H H CH₂ H H H OTf brown resin 6.034 H H O CH₃ H H H 137-138 6.035H H O H H F H 107-108 6.036 H H O OMe H H H 144-144 6.037 H H O Cl H H H150-151 6.038 H H O Cl H Cl H b) 6.039 H H O CHF₂ H H H 130-131 6.040 HH O H F H H 113-114 6.041 H H NC(O)Me H H H H 160-161 a)¹H-NMR (300 MHz,CDCl₃) 3.39 (2H, t); 3.98 (2H, m); 5.44 (1H, t, J = 8); 5.79 (1H, ddd, J= 49, 8, 6); 7.50 4H, m). b)¹H-NMR (300 MHz CDCl₃) 3.34 (2H, t); 3.88(2H, m); 4.38 (NH, b), 4.52 (1H, m); 4.80 (1H, m), 5.40 (1H, m), 7.24(4H, m).

TABLE 7 Characterising Data

Cpd.No R1 R5 R4a R4c R4d R¹⁰ isomer Mp [° C.] 7.001 H H Cl H H OH115-117 7.002 H H H H H NHBoc  63-64 7.003 H H H H H N═CMe₂ oil 7.004 HH H H H N(Ac)₂  91-92 7.005 H H H H H NHAc solid 7.006 H H F H H OH142-143 7.007 H H H H H OH white crystals 7.008 H Me H H H OH cis178-179 7.009 H Me H H H OH trans white crystals 7.010 H H Me H H OH 1837.011 H H H H H Me orange oil 7.012 H H H H H OMe orange oil 7.013 H H HH H NH₂ 103-105

TABLE 8 Characterising Data

Cpd.No R1 R2 Y R4a R4c R4d R¹⁰ isomer Mp [° C.] 8.001 H H CH₂ Br H Me2-thiazolyl white solid 8.002 H H CH₂ Me H Br 2-thiazolyl 176-181 8.003H H O H H H 2-thiazolyl beige crystals 8.004 H H CHMe H H H Boc 187-88.005 H H CHMe H H H thexylMe₂Si orange solid 8.006 H H CHMe H H HiPr₃Si solid 8.007 Me Me CH₂ H H H 2-thiazolyl 162-3 8.008 H H CH₂ H HEt 2-thiazolyl 111 8.009 H H CH₂ H H Me 2-thiazolyl 125 8.010 H H C═O FF H 2-thiazolyl 150-162 8.011 H H C═O H H H 2-thiazolyl 188 8.012 H HCHOH F F H 2-thiazolyl white foam 8.013 H H CH₂ F H H 2-thiazolyl 152-38.014 iPr H CH₂ H H H Boc cis oil 8.015 H H CH₂ m(CF₃)PhO H H CN resin8.016 H H CH₂ I H H Boc oil 8.017 H H CH₂ H H H CN  90-91 8.018 H H CH₂F H H CN  99-100 8.019 H H CH₂ OCHF₂ H H CN resin 8.020 H H CHOBoc F F HMe Cis 101-105 8.021 H H CHOH F F H Me Cis 170-173 8.022 H H CHOH F F HBoc Cis 119 8.023 H H C═O F F H Boc 158 8.024 H H CH₂ OCHF₂ H H CN solid8.025 H H CH₂ F H H acetyl solid 8.026 H H CH₂ Me H H CN resin 8.027 H HCH₂ NO₂ H H CN solid 8.028 H H CH₂ 3-CF₃-phenyl H H CN resin 8.029 H HCH₂ PhCC H H CN solid 8.030 H H CH₂ I H H CN solid 8.031 H H CH₂ Me H Hacetyl resin 8.032 H H CH₂ CHF₂ H H CN solid 8.033 H H CH₂ H H H Me₂NCO—resin 8.034 H H CH₂ F H H Me₂NCO resin 8.035 H H CH₂ I H H MeOCH₂ oil

Characterising Data-9

Mp [° C.] or Cpd. retention No. Y R4a R4c Isomer time^(a) 9.001CHOC(CF₃)Ph₂ F F cis  96-103 9.002 C═NOiBu F F 0.85 9.003C═NOCH₂(2,4,5-Cl₃Ph) F F 1.27 9.004 C═NOBn F F 0.95 9.005C═NNHC(O)(1-Me-3-CF₃- pyrazol-4-yl) F F 0.47 9.006 C═NNHC(O)NHPh F F0.92 9.007 C═NO-allyl F F 0.43 9.008 C═NNHC(O)OPh F F 0.43 9.009C═NNHSO₂Ph F F 0.79 9.010 C═NOtBu F F 1.00 9.011 C═NNHC(O)(benzo[1,2,5]thiadiazole-5-yl) F F 0.31 9.012 C═NO-pentafluorophenyl F F 1.13 9.013C═NNHC(S)NHiPr F F 0.83 9.014 C═NNHSO₂Me F F 0.17 9.015 C═NNHC(S)NHMe FF 0.18 9.016 C═NNHC(O)(2-benzylthio- phenyl) F F 1.01 9.017 C═NOnBu F F0.91 9.018 C═NNHTroc F F 0.85 9.019 C═NOEt F F 0.25 9.020 C═CH₂ F FSolid 9.021 C═CF₂ H H 106-108 9.022 C═NOH F F Decomp. 155 9.023 C═NOMe FF 104-114 ^(a)On a Waters 2795 HPLC using an Atlantis dC18 3ym, 3 x 20mm column two mobile phases were used. Eluant A contained 90% water, 10%MeCN, 0.1% formic acid. Eluant B contained 0.1% formic acid in MeCN. Forthe first 2.5 min a linear gradient change of eluant was made from 90%eluant A/10% eluant B to 100% eluant B. Then 100% eluant B was used. Theflow rate was 1.7 ml/min throughout. Compounds were detected by UV atusing a diode array measuring wavelengths between 200 nm and 400 nm.

Characterising Data-10

retention Cpd.No R¹⁰ time^(a) 10.001 C(O)(2,5-dimethyl-furan-3-yl) 1.0210.002 C(O)(1,3-dimethyl-pyrazol-5-yl) 1.05 10.003 C(O)CH₂OBn 1.5810.004 C(O)OnBu 0.78 10.005 C(O)NEt₂ 0.42 10.006 C(O)iPr 0.70 10.007C(O)NPh₂ 1.28 10.008 C(O)n-heptyl 1.57 10.009 C(O)-2-furyl 0.63 10.010C(O)CH═CH(p-nitrophenyl) 1.69 10.011 C(O)Et 0.36 10.012 C(O)OPh 0.8110.013 C(O)cyclopropyl 0.39 10.014 C(O)Ph 1.15 10.015 C(O)OMe 0.1810.016 C(O)-1-piperidyl 0.70 10.017 C(O)-3,5-dimethyl-isoxazol-4-yl 1.4710.018 C(O)isopropenyl 0.27 10.019 C(O)—O-isopropenyl 0.33 10.020C(O)OEt 0.49 10.021 C(O)CH₂C(O)OEt 1.56 10.022 C(O)CH₂-2-thienyl 1.3310.023 benzyl Oil 10.024 CH₂OMe Oil 10.025 C(O)Me 86-97 10.0263-methoxybenzyl Oil ^(a)On a Waters 2795 HPLC using an Atlantis dC183ym, 3 x 20 mm column two mobile phases were used. Eluant A contained90% water, 10% MeCN, 0.1% formic acid. Eluant B contained 0.1% formicacid in MeCN. For the first 2.5 min a linear gradient change of eluantwas made from 90% eluant A /10% eluant B to 100% eluant B. Then 100%eluant B was used. The flow rate was 1.7 ml/min throughout. Compoundswere detected by UV at using a diode array measuring wavelengths between200 nm and 400 nm.

Characterising Data-11

Cpd.No Td Te Tf Y R₁ R₂ R₁₀ Mp [° C.] 11.001 S CH CH CH₂ H H H 144-14511.002 S CH CH CH₂ H H CH₂C≡CH a) 11.003 CH CH S CH₂ H H H 146-14711.004 S CMe CH CH₂ H H H 170-172 11.005 S CH CH CH₂ H H C(O)NM2₂ b)a)¹H-NMR (300 MHz CDCl₃) 2.21 (1H, t), 2.38 (1H, m), 2.83 (2H, m), 3.03(1H, m), 3.32 (2H, m); 3.56 (2H, m), 4.16 (2H, m); 4.56 (1H, m), 6,83(1H, d), 7.13 (1H, d). b)¹H-NMR (300 MHz CDCl₃) 2.38 (1H, m), 2.82 (2H,m), 2.90 (6H, S), 3.02 (1H, m), 3.20 (2H, m); 3.80 (2H, m), 4.16 (2H,m); 4.53 (1H, m), 6,82 (1H, d), 7.13 (1H, d).

Characterising Data-12

Cpd.No R1 Mp [° C.] 12.001 nBu Cis 91-94 12.002 nBu Trans 80-82 12.003COnPr Cis 105-106 12.004 F Cis Resin 12.005 C(O)Me Cis 128-129 12.006C(O)Et Cis 104-105 12.007 CH₂OH Trans144-145 12.008 OAc Trans Oil 12.009CH₂OAc Trans Resin 12.010 OMe Trans 96-98 12.011 OBz Trans 117-11912.012 CH₂OMe Trans Resin 12.013 CH₂OMs Trans Solid 12.014 CH₂OBn Trans140 Decomp. 12.015 CH₂SMe trans resin 12.016 CH₂Ocinnamyl Trans Oil12.017 CH₂OCH₂CO₂tBu Trans Oil 12.018 CH₂S(O)Me trans resin 12.019CH₂SO₂Me trans resin 12.020 SePh Trans Oil 12.021^(g)) CH₂SH Trans141-147 12.022 CH₂SePH Trans 99-101 12.023 CH₂SC(S)NEt₂ Trans Resin12.024 CH₂CN Trans 110-113 12.025 CH₂SCN Trans Oil 12.026 CH₂OpFPh Trans127-133 12.027 CH₂OPh Trans 100 Decomp. 12.028 CH₂SC(S)OEt Trans Resin12.029 CO₂H trans solid ^(g))TFA salt

The compounds of the invention may be made by a variety of methods, forexample those described in Tet. 2006, 62, 513

The compounds of the formula I can be prepared from amines of theformula II.

Methods for performing this transformation include A. Treatment withhaloethylisothiocyanate as used in Examples 3, 8 (step 6) and 9 (step 6)using the procedures of for example DE 3133918, Indian J. Chem. 1984,23B, 1243-57 or Heterocycles 1990, 30, 463-9; and B. Treatment with2-methylthio-2-thiazoline as described in Example 1 following theprocedures in for example J. Am. Chem. Soc. 1958, 80, 3339, J. Org.Chem. 1961, 26, 1666 or J. Med. Chem. 1982, 25, 735-42.

In a further aspect of the invention there is provided the use of2-alkoxy-2-thiazolines, or 2-aryloxy-2-thiazolines of the formula (III)

where R_(z) is optionally substituted alkyl and aryl as reagents for thepreparation of compounds of formula I. The transformation using III isdescribed in Examples 2 and 4. The use of these reagents offersconsiderable advantages over the use of the corresponding2-methylthio-2-thiazoline (see Example 3), as the reaction takes placeat lower temperature (see Examples 2 and 4).

Additional methods for converting amines into aminothiazolines aredescribed in the literature and can be adapted for transforming amines(II) into aminothiazolines (I). Thus the amines can be converted tothioureas and then treated with 1,2-dibromoethane as described in forexample J. Het. Chem. 1986, 23, 1439-42, or also in Ind. J. Chem 1983,22B, 249-51, or the amines can be treated at higher temperature with an2-amino-thiazoline following the method of CH 667652.

Alternatively the amines can be converted to thioureas and then treatedwith 2-bromo-ethylamine as described in Bioorg. Med. Chem. 2001, 9,2025.

As a further alternative the amines (II) can be converted intoisothiocyanates (VI) and then treated with 2-halo-ethylamine asdescribed in for example J. Org. Chem. 1983, 48, 3901-8 or also in J.Med. Chem. 1987, 30, 1955-62.

The amines (II_(i)) can be used to make 2-hydroxyethyl-thioureas(VII_(i)), according to methods found in Houben-Weyl E4, (1983) 484, forexample using in a first step thiophosgene, and then in a second step2-hydroxyethylamine. The thioureas (VII_(ii)) can be prepared from theisothiocyanates (VI) as described in Example 11. Each of these thioureascan be cyclised to the corresponding thiazolines (I), for example withacid as described for example in U.S. Pat. No. 4,398,028 and in Tet.Lett. 2003, 44, 795-9, or with Ph₃P and DEAD as described in Tet. Lett.1999, 40, 3125 and also described in Example 11. If R¹⁰ is H, then (II)and (II_(i)) are identical, (VII₁) and VII_(ii)) are identical, and(I_(i)), (I_(ii)) and (Iiii) are tautomers of the same compound.

The amines (II) can be converted into isothiocyanates (VI) and thentreated with aziridine to the corresponding thioureas which can then berearranged to the aminothiazolines as described for example in Arch.Pharm. 1958, 291, 457 or also in J. Amer. Chem. Soc. 1961, 83, 2570.

Compounds of the formula I and R⁹ and R¹⁰ are H can be prepared fromketones of the formula IV.

Thus the ketone and 2-aminothiazoline are treated with an agent, whichadsorbs, absorbs, or reacts with water such as titanium tetraalkoxide toyield an imine or enamine intermediate, which is then treated with areducing agent such as sodium borohydride to yield the aminothiazoline(I). An example of this method is described in Example 8. The reactionof ketones with primary amines using drying and reducing agents to formsecondary amines is known as reductive amination and is described in forexample Organic Reactions 2002, 59, 1-714.

Compounds of the formula I where R¹⁰ is not H can be prepared fromcompounds of the formula I where R¹⁰ is hydrogen, by treatment with asuitable derivatising agent. When R¹⁰ is an acyl group, acylating agentscan be used. When R¹⁰ is an alkyl group, alkylating agents can be used.When R¹⁰ is a sulfenyl group, sulfenylating agents can be used.Derivatisation is this manner is well known. Descriptions and methodsfor these transformations can be found in T. W. Greene and P. G. M. Wuts“Protective Groups in Organic Synthesis” 3^(rd) Edition, Wiley, N.Y,1999. The group R¹⁰ can also be introduced via a synthetic precursor ofcompounds of the formula I, for example via an amine of the formulaII_(i), or via a N—R¹⁰ substituted hydroxyethylamine.

Amines of the formula (II) can be prepared in various ways. Thus ketones(IV) can be converted into amines of the formula (II) wherein R⁹ is H.One method for this transformation involves reductive amination forexample according to Example 7 and Tetrahedron 2004, 60, 1463-71. Thistransformation can also be performed in two steps via an oxime andsubsequent reduction as exemplified in Examples 9 and intermediateexample 1.

Amines of the formula (II) can also be prepared from carboxylic acids(V), by a Curtius degradation as shown in Example 5.

Amines of formula (II), wherein Y is oxygen are partially known or maybe prepared by the known methods as described in Chimica Acta Turica,13(3), 403-412 (1985) and Farmaco, Edizione Scientifica, 43(7-8),643-655 (1988).

Certain of the isothiocyanates of the formula (VI) are new and are partof this invention.

The novel compounds are those of the formula VIA

where R₁, R₄a, R₄b, R₄c and R₄d are each independently H, halogen, C₁-C₆alkyl or C₁-C₆ haloalkyl, and where at least one of these substituentmust be different to H.

Preferred compounds of the formula (VIA) are those wherein the valuesR₁, R₄a, R₄b, R₄c and R₄d are given in Table 9.

TABLE 9 Compound No R1 R₄a R₄b R₄c R₄d VIA-1 H F H H H VIA-2 H CH₃ H H HVIA-3 H F H F H VIA-4 H F H CH₃ H VIA-5 H F H H F VIA-6 H CH₃ H F HVIA-7 F H H H H VIA-8 CH₃ H H H H VIA-9 F F H H H VIA-10 F CH₃ H H HVIA-11 F F H F H VIA-12 F F H CH₃ H VIA-13 F F H H F VIA-14 CH₃ F H H HVIA-15 CH₃ CH₃ H H H VIA-16 CH₃ F H F H VIA-17 CH₃ F H CH₃ H VIA-18 CH₃F H H F

The compounds of formula (I) can be used to combat and controlinfestations of insect pests such as Lepidoptera, Diptera, Hemiptera,Thysanoptera, Orthoptera, Dictyoptera, Coleoptera, Siphonaptera,Hymenoptera and Isoptera and also other invertebrate pests, for example,acarine, nematode and mollusc pests. Insects, acarines, nematodes andmolluscs are hereinafter collectively referred to as pests. The pestswhich may be combated and controlled by the use of the inventioncompounds include those pests associated with agriculture (which termincludes the growing of crops for food and fibre products), horticultureand animal husbandry, companion animals, forestry and the storage ofproducts of vegetable origin (such as fruit, grain and timber); thosepests associated with the damage of man-made structures and thetransmission of diseases of man and animals; and also nuisance pests(such as flies).

Examples of pest species which may be controlled by the compounds offormula (I) include: Myzus persicae (aphid), Aphis gossypii (aphid),Aphis fabae (aphid), Lygus spp. (capsids), Dysdercus spp. (capsids),Nilaparvata lugens (planthopper), Nephotettixc incticeps (leafhopper),Nezara spp. (stinkbugs), Euschistus spp. (stinkbugs), Leptocorisa spp.(stinkbugs), Frankliniella occidentalis (thrip), Thrips spp. (thrips),Leptinotarsa decemlineata (Colorado potato beetle), Anthonomus grandis(boll weevil), Aonidiella spp. (scale insects), Trialeurodes spp. (whiteflies), Bemisia tabaci (white fly), Ostrinia nubilalis (European cornborer), Spodoptera littoralis (cotton leafworm), Heliothis virescens(tobacco budworm), Helicoverpa armigera (cotton bollworm), Helicoverpazea (cotton bollworm), Sylepta derogata (cotton leaf roller), Pierisbrassicae (white butterfly), Plutella xylostella (diamond back moth),Agrotis spp. (cutworms), Chilo suppressalis (rice stem borer), Locustamigratoria (locust), Chortiocetes terminifera (locust), Diabrotica spp.(rootworms), Panonychus ulmi (European red mite), Panonychus citri(citrus red mite), Tetranychus urticae (two-spotted spider mite),Tetranychus cinnabarinus (carmine spider mite), Phyllocoptruta oleivora(citrus rust mite), Polyphagotarsonemus latus (broad mite), Brevipalpusspp. (flat mites), Boophilus microplus (cattle tick), Dermacentorvariabilis (American dog tick), Ctenocephalides fells (cat flea),Liriomyza spp. (leafminer), Musca domestica (housefly), Aedes aegypti(mosquito), Anopheles spp. (mosquitoes), Culex spp. (mosquitoes),Lucillia spp. (blowflies), Blattella germanica (cockroach), Periplanetaamericana (cockroach), Blatta orientalis (cockroach), termites of theMastotermitidae (for example Mastotermes spp.), the Kalotermitidae (forexample Neotermes spp.), the Rhinotermitidae (for example Coptotermesformosanus, Reticulitermes flavipes, R. speratu, R. virginicus, R.hesperus, and R. santonensis) and the Termitidae (for exampleGlobitermes sulphureus), Solenopsis geminata (fire ant), Monomoriumpharaonis (pharaoh's ant), Damalinia spp. and Linognathus spp. (bitingand sucking lice), and Deroceras reticulatum (slug).

The invention therefore provides a method of combating and controllinginsects, acarines, or molluscs which comprises applying aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I), or a composition containing acompound of formula (I), to a pest, a locus of pest, or to a plantsusceptible to attack by a pest, The compounds of formula (I) arepreferably used against insects or acarines.

The term “plant” as used herein includes seedlings, bushes and trees.

In order to apply a compound of formula (I) as an insecticide,acaricide, nematicide or molluscicide to a pest, a locus of pest, or toa plant susceptible to attack by a pest, a compound of formula (I) isusually formulated into a composition which includes, in addition to thecompound of formula (I), a suitable inert diluent or carrier and,optionally, a surface active agent (SFA). SFAs are chemicals which areable to modify the properties of an interface (for example,liquid/solid, liquid/air or liquid/liquid interfaces) by lowering theinterfacial tension and thereby leading to changes in other properties(for example dispersion, emulsification and wetting). It is preferredthat all compositions (both solid and liquid formulations) comprise, byweight, 0.0001 to 95%, more preferably 1 to 85%, for example 5 to 60%,of a compound of formula (I). The composition is generally used for thecontrol of pests such that a compound of formula (I) is applied at arate of from 0.1 g to 10 kg per hectare, preferably from 1 g to 6 kg perhectare, more preferably from 1 g to 1 kg per hectare.

When used in a seed dressing, a compound of formula (I) is used at arate of 0.0001 g to 10 g (for example 0.001 g or 0.05 g), preferably0.005 g to 10 g, more preferably 0.005 g to 4 g, per kilogram of seed.

In another aspect the present invention provides an insecticidal,acaricidal, nematicidal or molluscicidal composition comprising aninsecticidally, acaricidally, nematicidally or molluscicidally effectiveamount of a compound of formula (I) and a suitable carrier or diluenttherefor. The composition is preferably an insecticidal, acaricidal,nematicidal or molluscicidal composition.

In a still further aspect the invention provides a method of combatingand controlling pests at a locus which comprises treating the pests orthe locus of the pests with an insecticidally, acaricidally,nematicidally or molluscicidally effective amount of a compositioncomprising a compound of formula (I). The compounds of formula (I) arepreferably used against insects, acarines or nematodes.

The compositions can be chosen from a number of formulation types,including dustable powders (DP), soluble powders (SP), water solublegranules (SG), water dispersible granules (WG), wettable powders (WP),granules (GR) (slow or fast release), soluble concentrates (SL), oilmiscible liquids (OL), ultra low volume liquids (UL), emulsifiableconcentrates (EC), dispersible concentrates (DC), emulsions (both oil inwater (EW) and water in oil (EO)), micro-emulsions (ME), suspensionconcentrates (SC), aerosols, fogging/smoke formulations, capsulesuspensions (CS) and seed treatment formulations. The formulation typechosen in any instance will depend upon the particular purpose envisagedand the physical, chemical and biological properties of the compound offormula (I).

Dustable powders (DP) may be prepared by mixing a compound of formula(I) with one or more solid diluents (for example natural clays, kaolin,pyrophyllite, bentonite, alumina, montmorillonite, kieselguhr, chalk,diatomaceous earths, calcium phosphates, calcium and magnesiumcarbonates, sulphur, lime, flours, talc and other organic and inorganicsolid carriers) and mechanically grinding the mixture to a fine powder.

Soluble powders (SP) may be prepared by mixing a compound of formula (I)with one or more water-soluble inorganic salts (such as sodiumbicarbonate, sodium carbonate or magnesium sulphate) or one or morewater-soluble organic solids (such as a polysaccharide) and, optionally,one or more wetting agents, one or more dispersing agents or a mixtureof said agents to improve water dispersibility/solubility. The mixtureis then ground to a fine powder. Similar compositions may also begranulated to form water soluble granules (SG).

Wettable powders (WP) may be prepared by mixing a compound of formula(I) with one or more solid diluents or carriers, one or more wettingagents and, preferably, one or more dispersing agents and, optionally,one or more suspending agents to facilitate the dispersion in liquids.The mixture is then ground to a fine powder. Similar compositions mayalso be granulated to form water dispersible granules (WG).

Granules (GR) may be formed either by granulating a mixture of acompound of formula (I) and one or more powdered solid diluents orcarriers, or from pre-formed blank granules by absorbing a compound offormula (I) (or a solution thereof, in a suitable agent) in a porousgranular material (such as pumice, attapulgite clays, fuller's earth,kieselguhr, diatomaceous earths or ground corn cobs) or by adsorbing acompound of formula (I) (or a solution thereof, in a suitable agent) onto a hard core material (such as sands, silicates, mineral carbonates,sulphates or phosphates) and drying if necessary. Agents which arecommonly used to aid absorption or adsorption include solvents (such asaliphatic and aromatic petroleum solvents, alcohols, ethers, ketones andesters) and sticking agents (such as polyvinyl acetates, polyvinylalcohols, dextrins, sugars and vegetable oils). One or more otheradditives may also be included in granules (for example an emulsifyingagent, wetting agent or dispersing agent).

Dispersible Concentrates (DC) may be prepared by dissolving a compoundof formula (I) in water or an organic solvent, such as a ketone, alcoholor glycol ether. These solutions may contain a surface active agent (forexample to improve water dilution or prevent crystallisation in a spraytank).

Emulsifiable concentrates (EC) or oil-in-water emulsions (EW) may beprepared by dissolving a compound of formula (I) in an organic solvent(optionally containing one or more wetting agents, one or moreemulsifying agents or a mixture of said agents). Suitable organicsolvents for use in ECs include aromatic hydrocarbons (such asalkylbenzenes or alkylnaphthalenes, exemplified by SOLVESSO 100,SOLVESSO 150 and SOLVESSO 200; SOLVESSO is a Registered Trade Mark),ketones (such as cyclohexanone or methylcyclohexanone) and alcohols(such as benzyl alcohol, furfuryl alcohol or butanol),N-alkylpyrrolidones (such as N-methylpyrrolidone or N-octylpyrrolidone),dimethyl amides of fatty acids (such as C₈-C₁₀ fatty acid dimethylamide)and chlorinated hydrocarbons. An EC product may spontaneously emulsifyon addition to water, to produce an emulsion with sufficient stabilityto allow spray application through appropriate equipment. Preparation ofan EW involves obtaining a compound of formula (I) either as a liquid(if it is not a liquid at room temperature, it may be melted at areasonable temperature, typically below 70° C.) or in solution (bydissolving it in an appropriate solvent) and then emulsifiying theresultant liquid or solution into water containing one or more SFAs,under high shear, to produce an emulsion. Suitable solvents for use inEWs include vegetable oils, chlorinated hydrocarbons (such aschlorobenzenes), aromatic solvents (such as alkylbenzenes oralkylnaphthalenes) and other appropriate organic solvents which have alow solubility in water.

Microemulsions (ME) may be prepared by mixing water with a blend of oneor more solvents with one or more SFAs, to produce spontaneously athermodynamically stable isotropic liquid formulation. A compound offormula (I) is present initially in either the water or the solvent/SFAblend. Suitable solvents for use in MEs include those hereinbeforedescribed for use in in ECs or in EWs. An ME may be either anoil-in-water or a water-in-oil system (which system is present may bedetermined by conductivity measurements) and may be suitable for mixingwater-soluble and oil-soluble pesticides in the same formulation. An MEis suitable for dilution into water, either remaining as a microemulsionor forming a conventional oil-in-water emulsion.

Suspension concentrates (SC) may comprise aqueous or non-aqueoussuspensions of finely divided insoluble solid particles of a compound offormula (I). SCs may be prepared by ball or bead milling the solidcompound of formula (I) in a suitable medium, optionally with one ormore dispersing agents, to produce a fine particle suspension of thecompound. One or more wetting agents may be included in the compositionand a suspending agent may be included to reduce the rate at which theparticles settle. Alternatively, a compound of formula (I) may be drymilled and added to water, containing agents hereinbefore described, toproduce the desired end product.

Aerosol formulations comprise a compound of formula (I) and a suitablepropellant (for example n-butane). A compound of formula (I) may also bedissolved or dispersed in a suitable medium (for example water or awater miscible liquid, such as n-propanol) to provide compositions foruse in non-pressurised, hand-actuated spray pumps.

A compound of formula (I) may be mixed in the dry state with apyrotechnic mixture to form a composition suitable for generating, in anenclosed space, a smoke containing the compound.

Capsule suspensions (CS) may be prepared in a manner similar to thepreparation of EW formulations but with an additional polymerisationstage such that an aqueous dispersion of oil droplets is obtained, inwhich each oil droplet is encapsulated by a polymeric shell and containsa compound of formula (I) and, optionally, a carrier or diluenttherefor. The polymeric shell may be produced by either an interfacialpolycondensation reaction or by a coacervation procedure. Thecompositions may provide for controlled release of the compound offormula (I) and they may be used for seed treatment. A compound offormula (I) may also be formulated in a biodegradable polymeric matrixto provide a slow, controlled release of the compound.

A composition may include one or more additives to improve thebiological performance of the composition (for example by improvingwetting, retention or distribution on surfaces; resistance to rain ontreated surfaces; or uptake or mobility of a compound of formula (I)).Such additives include surface active agents, spray additives based onoils, for example certain mineral oils or natural plant oils (such assoy bean and rape seed oil), and blends of these with otherbio-enhancing adjuvants (ingredients which may aid or modify the actionof a compound of formula (I)).

A compound of formula (I) may also be formulated for use as a seedtreatment, for example as a powder composition, including a powder fordry seed treatment (DS), a water soluble powder (SS) or a waterdispersible powder for slurry treatment (WS), or as a liquidcomposition, including a flowable concentrate (FS), a solution (LS) or acapsule suspension (CS). The preparations of DS, SS, WS, FS and LScompositions are very similar to those of, respectively, DP, SP, WP, SCand DC compositions described above. Compositions for treating seed mayinclude an agent for assisting the adhesion of the composition to theseed (for example a mineral oil or a film-forming barrier).

Wetting agents, dispersing agents and emulsifying agents may be surfaceSFAs of the cationic, anionic, amphoteric or non-ionic type.

Suitable SFAs of the cationic type include quaternary ammonium compounds(for example cetyltrimethyl ammonium bromide), imidazolines and aminesalts.

Suitable anionic SFAs include alkali metals salts of fatty acids, saltsof aliphatic monoesters of sulphuric acid (for example sodium laurylsulphate), salts of sulphonated aromatic compounds (for example sodiumdodecylbenzenesulphonate, calcium dodecylbenzenesulphonate,butylnaphthalene sulphonate and mixtures of sodium di-isopropyl- andtri-isopropyl-naphthalene sulphonates), ether sulphates, alcohol ethersulphates (for example sodium laureth-3-sulphate), ether carboxylates(for example sodium laureth-3-carboxylate), phosphate esters (productsfrom the reaction between one or more fatty alcohols and phosphoric acid(predominately mono-esters) or phosphorus pentoxide (predominatelydi-esters), for example the reaction between lauryl alcohol andtetraphosphoric acid; additionally these products may be ethoxylated),sulphosuccinamates, paraffin or olefine sulphonates, taurates andlignosulphonates.

Suitable SFAs of the amphoteric type include betaines, propionates andglycinates.

Suitable SFAs of the non-ionic type include condensation products ofalkylene oxides, such as ethylene oxide, propylene oxide, butylene oxideor mixtures thereof, with fatty alcohols (such as oleyl alcohol or cetylalcohol) or with alkylphenols (such as octylphenol, nonylphenol oroctylcresol); partial esters derived from long chain fatty acids orhexitol anhydrides; condensation products of said partial esters withethylene oxide; block polymers (comprising ethylene oxide and propyleneoxide); alkanolamides; simple esters (for example fatty acidpolyethylene glycol esters); amine oxides (for example lauryl dimethylamine oxide); and lecithins.

Suitable suspending agents include hydrophilic colloids (such aspolysaccharides, polyvinylpyrrolidone or sodium carboxymethylcellulose)and swelling clays (such as bentonite or attapulgite).

A compound of formula (I) may be applied by any of the known means ofapplying pesticidal compounds. For example, it may be applied,formulated or unformulated, to the pests or to a locus of the pests(such as a habitat of the pests, or a growing plant liable toinfestation by the pests) or to any part of the plant, including thefoliage, stems, branches or roots, to the seed before it is planted orto other media in which plants are growing or are to be planted (such assoil surrounding the roots, the soil generally, paddy water orhydroponic culture systems), directly or it may be sprayed on, dustedon, applied by dipping, applied as a cream or paste formulation, appliedas a vapour or applied through distribution or incorporation of acomposition (such as a granular composition or a composition packed in awater-soluble bag) in soil or an aqueous environment.

A compound of formula (I) may also be injected into plants or sprayedonto vegetation using electrodynamic spraying techniques or other lowvolume methods, or applied by land or aerial irrigation systems.

Compositions for use as aqueous preparations (aqueous solutions ordispersions) are generally supplied in the form of a concentratecontaining a high proportion of the active ingredient, the concentratebeing added to water before use. These concentrates, which may includeDCs, SCs, ECs, EWs, MEs SGs, SPs, WPs, WGs and CSs, are often requiredto withstand storage for prolonged periods and, after such storage, tobe capable of addition to water to form aqueous preparations whichremain homogeneous for a sufficient time to enable them to be applied byconventional spray equipment. Such aqueous preparations may containvarying amounts of a compound of formula (I) (for example 0.0001 to 10%,by weight) depending upon the purpose for which they are to be used.

A compound of formula (I) may be used in mixtures with fertilisers (forexample nitrogen-, potassium- or phosphorus-containing fertilisers).Suitable formulation types include granules of fertiliser. The mixturessuitably contain up to 25% by weight of the compound of formula (I).

The invention therefore also provides a fertiliser compositioncomprising a fertiliser and a compound of formula (I).

The compositions of this invention may contain other compounds havingbiological activity, for example micronutrients or compounds havingfungicidal activity or which possess plant growth regulating,herbicidal, insecticidal, nematicidal or acaricidal activity.

The compound of formula (I) may be the sole active ingredient of thecomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may: provide a composition having a broader spectrum ofactivity or increased persistence at a locus; synergise the activity orcomplement the activity (for example by increasing the speed of effector overcoming repellency) of the compound of formula (I); or help toovercome or prevent the development of resistance to individualcomponents. The particular additional active ingredient will depend uponthe intended utility of the composition. Examples of suitable pesticidesinclude the following:

a) Pyrethroids, such as permethrin, cypermethrin, fenvalerate,esfenvalerate, deltamethrin, cyhalothrin (in particularlambda-cyhalothrin), bifenthrin, fenpropathrin, cyfluthrin, tefluthrin,fish safe pyrethroids (for example ethofenprox), natural pyrethrin,tetramethrin, s-bioallethrin, fenfluthrin, prallethrin or5-benzyl-3-furylmethyl-(E)-(1R,3S)-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate;b) Organophosphates, such as, profenofos, sulprofos, acephate, methylparathion, azinphos-methyl, demeton-s-methyl, heptenophos, thiometon,fenamiphos, monocrotophos, profenofos, triazophos, methamidophos,dimethoate, phosphamidon, malathion, chlorpyrifos, phosalone, terbufos,fensulfothion, fonofos, phorate, phoxim, pirimiphos-methyl,pirimiphos-ethyl, fenitrothion, fosthiazate or diazinon;c) Carbamates (including aryl carbamates), such as pirimicarb,triazamate, cloethocarb, carbofuran, furathiocarb, ethiofencarb,aldicarb, thiofurox, carbosulfan, bendiocarb, fenobucarb, propoxur,methomyl or oxamyl;d) Benzoyl ureas, such as diflubenzuron, triflumuron, hexaflumuron,flufenoxuron or chlorfluazuron;e) Organic tin compounds, such as cyhexatin, fenbutatin oxide orazocyclotin;f) Pyrazoles, such as tebufenpyrad and fenpyroximate;g) Macrolides, such as avermectins or milbemycins, for exampleabamectin, emamectin benzoate, ivermectin, milbemycin, spinosad orazadirachtin;h) Hormones or pheromones;i) Organochlorine compounds such as endosulfan, benzene hexachloride,DDT, chlordane or dieldrin;j) Amidines, such as chlordimeform or amitraz;k) Fumigant agents, such as chloropicrin, dichloropropane, methylbromide or metam;l) Chloronicotinyl compounds such as imidacloprid, thiacloprid,acetamiprid, nitenpyram or thiamethoxam;m) Diacylhydrazines, such as tebufenozide, chromafenozide ormethoxyfenozide;n) Diphenyl ethers, such as diofenolan or pyriproxifen;

o) Indoxacarb; p) Chlorfenapyr; or q) Pymetrozine.

In addition to the major chemical classes of pesticide listed above,other pesticides having particular targets may be employed in thecomposition, if appropriate for the intended utility of the composition.For instance, selective insecticides for particular crops, for examplestemborer specific insecticides (such as cartap) or hopper specificinsecticides (such as buprofezin) for use in rice may be employed.Alternatively insecticides or acaricides specific for particular insectspecies/stages may also be included in the compositions (for exampleacaricidal ovo-larvicides, such as clofentezine, flubenzimine,hexythiazox or tetradifon; acaricidal motilicides, such as dicofol orpropargite; acaricides, such as bromopropylate or chlorobenzilate; orgrowth regulators, such as hydramethylnon, cyromazine, methoprene,chlorfluazuron or diflubenzuron).

Examples of fungicidal compounds which may be included in thecomposition of the invention are(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide(SSF-129),4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethyl-benzimidazole-1-sulphonamide,α-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-γ-butyrolactone,4-chloro-2-cyano-N,N-dimethyl-5-p-tolylimidazole-1-sulfonamide (IKF-916,cyamidazosulfamid),3-5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide(RH-7281, zoxamide),N-allyl-4,5-dimethyl-2-trimethylsilylthiophene-3-carboxamide (MON65500),N-(1-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy)propionamide(AC382042), N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,acibenzolar (CGA245704), alanycarb, aldimorph, anilazine, azaconazole,azoxystrobin, benalaxyl, benomyl, biloxazol, bitertanol, blasticidin S,bromuconazole, bupirimate, captafol, captan, carbendazim, carbendazimchlorhydrate, carboxin, carpropamid, carvone, CGA41396, CGA41397,chinomethionate, chlorothalonil, chlorozolinate, clozylacon, coppercontaining compounds such as copper oxychloride, copper oxyquinolate,copper sulphate, copper tallate and Bordeaux mixture, cymoxanil,cyproconazole, cyprodinil, debacarb, di-2-pyridyl disulphide1,1′-dioxide, dichlofluanid, diclomezine, dicloran, diethofencarb,difenoconazole, difenzoquat, diflumetorim, O,O-di-iso-propyl-5-benzylthiophosphate, dimefluazole, dimetconazole, dimethomorph, dimethirimol,diniconazole, dinocap, dithianon, dodecyl dimethyl ammonium chloride,dodemorph, dodine, doguadine, edifenphos, epoxiconazole, ethirimol,ethyl(Z)-N-benzyl-N([methyl(methyl-thioethylideneaminooxycarbonyl)amino]thio)-β-alaninate,etridiazole, famoxadone, fenamidone (RPA407213), fenarimol,fenbuconazole, fenfuram, fenhexamid (KBR2738), fenpiclonil, fenpropidin,fenpropimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, fluoroimide, fluquinconazole,flusilazole, flutolanil, flutriafol, folpet, fuberidazole, furalaxyl,furametpyr, guazatine, hexaconazole, hydroxyisoxazole, hymexazole,imazalil, imibenconazole, iminoctadine, iminoctadine triacetate,ipconazole, iprobenfos, iprodione, iprovalicarb (SZX0722), isopropanylbutyl carbamate, isoprothiolane, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, maneb, mefenoxam, mepanipyrim, mepronil,metalaxyl, metconazole, metiram, metiram-zinc, metominostrobin,myclobutanil, neoasozin, nickel dimethyldithiocarbamate,nitrothal-isopropyl, nuarimol, ofurace, organomercury compounds,oxadixyl, oxasulfuron, oxolinic acid, oxpoconazole, oxycarboxin,pefurazoate, penconazole, pencycuron, phenazin oxide, phosetyl-A1,phosphorus acids, phthalide, picoxystrobin (ZA1963), polyoxin D,polyram, probenazole, prochloraz, procymidone, propamocarb,propiconazole, propineb, propionic acid, pyrazophos, pyrifenox,pyrimethanil, pyroquilon, pyroxyfur, pyrroInitrin, quaternary ammoniumcompounds, quinomethionate, quinoxyfen, quintozene, sipconazole (F-155),sodium pentachlorophenate, spiroxamine, streptomycin, sulphur,tebuconazole, tecloftalam, tecnazene, tetraconazole, thiabendazole,thifluzamid, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl,thiram, timibenconazole, tolclofos-methyl, tolylfluanid, triadimefon,triadimenol, triazbutil, triazoxide, tricyclazole, tridemorph,trifloxystrobin (CGA279202), triforine, triflumizole, triticonazole,validamycin A, vapam, vinclozolin, zineb and ziram.

The compounds of formula (I) may be mixed with soil, peat or otherrooting media for the protection of plants against seed-borne,soil-borne or foliar fungal diseases.

Examples of suitable synergists for use in the compositions includepiperonyl butoxide, sesamex, safroxan and dodecyl imidazole.

Suitable herbicides and plant-growth regulators for inclusion in thecompositions will depend upon the intended target and the effectrequired.

An example of a rice selective herbicide which may be included ispropanil. An example of a plant growth regulator for use in cotton isPIX™.

Some mixtures may comprise active ingredients which have significantlydifferent physical, chemical or biological properties such that they donot easily lend themselves to the same conventional formulation type. Inthese circumstances other formulation types may be prepared. Forexample, where one active ingredient is a water insoluble solid and theother a water insoluble liquid, it may nevertheless be possible todisperse each active ingredient in the same continuous aqueous phase bydispersing the solid active ingredient as a suspension (using apreparation analogous to that of an SC) but dispersing the liquid activeingredient as an emulsion (using a preparation analogous to that of anEW). The resultant composition is a suspoemulsion (SE) formulation.

The invention is illustrated by the following Examples:

Mass spectra data were obtained for selected compounds of the followingexamples using

LCMS: LC5: 254 nm—gradient 10% A to 100% B A=H₂O+0.01% HCOOHB=CH₃CN/CH₃OH+0.01% HCOOH positive electrospray 150-1000 M/z.

EXAMPLE 1

This Example illustrates the preparation of compound No 2.002

Example 1

A solution of 1-aminoindane (0.5 ml, 3.87 mmol),2-methylthio-2-thiazoline (0.421 ml, 3.87 mmol), and methanesulfonicacid (0.251 ml, 3.87 mmol) in butanol (5 ml) was heated under reflux at125° C. bath temperature for 16 hours. The solvent was evaporated, thecrude product separated between HCl (2M) and diethyl ether. The organicphase was made basic with NaOH (32%) and the product extracted intodichloromethane, dried (MgSO₄) and evaporated to yield 912 mg of productas beige crystals m.p. 137° C.

EXAMPLE 2

This Example illustrates the preparation of compound No 2.002

A solution of 1-aminoindane (0.2 ml, 1.55 mmol), 2-methoxy-2-thiazoline(182 mg, 1.55 mmol), and methanesulfonic acid (0.050 ml, 0.77 mmol) inbutanol (1 ml) was left at room temperature for 15 days. The mixture wasshaken between NaOH (1M) and dichloromethane, and the organic phasedried (MgSO₄) and evaporated to yield 286 mg of product as beigecrystals m.p. 137° C.

EXAMPLE 3

This Example illustrates the preparation of compound No 2.019

A solution of 4-fluoro-1-indanamine (300 mg, 1.98 mmol) in THF (2.5 ml)was stirred at 0° C. A solution of chloroethyl isothiocyanate (0.200 ml,2.08 mmol) in THF (0.5 ml) was added, and the mixture stirred at roomtemperature overnight. The supernatant was decanted and the remainingcrystals washed twice with ether, dissolved in water, basified with NaOH(32%) and the product extracted into dichloromethane, dried (MgSO₄) andevaporated to leave a dark yellow solid, which was washed twice withether to yield the product as a fine white powder. m.p. 149° C.

EXAMPLE 4

This Example illustrates the preparation of compound number 6.011

A solution of 7-propyl-1-indanamine (184 mg, 1.05 mmol),2-(p-tolyloxy)-2-thiazoline (0.174 ml, 203 mg, 1.05 mmol) andmethansulfonic acid (0.034 ml, 50 mg, 0.527 mmol) in nBuOH (1 ml) washeated at 110° C. for 2 hours. The solvent was evaporated and themixture shaken with tBuOMe, NaOH (2M) and NaCl (satd). The product wastaken into HCl (2M), and after basification with NaOH (32%) back intotBuOMe, which was washed with NaCl (satd), dried (MgSO₄), and evaporatedto yield 272 mg as a syrup, which crystallised on standing. m.p. 72-75°C.

EXAMPLE 5

This Example illustrates the preparation of compound number 3.004.

Step 1

A solution of indane-1-carboxylic acid (4.1 g, 25.3 mmol) in THF (30 ml)was added in portions to a solution of lithium diisopropylamide in THF(2M, 27.8 ml, 55.6 mmol) with stirring at −20° C. The solution was thenstirred at 35° C. for 1 hour, then cooled again to −20° C. and asolution of methyl iodide (2.05 ml, 32.89 mmol) in THF (10 ml) wasadded. The light yellow solution was warmed at 35° C. for 4 hours beforeextracting between HCl (2M) and EtOAc to yield the crude product (4.5 g)as a brown oil. This mixture was cromatographed on HPLC withEtOAc/hexane to yield 1-methyl-1-indanecarboxylic acid (1 g) andrecovered starting material (700 mg)

Step 2

A solution of 1-methyl-1-indanecarboxylic acid (864 mg, 4.9 mmol),diphenylphosphoryl azide (1.3 ml, 6.02 mmol) and triethylamine (0.95 ml,6.87 mmol) in tBuOH (10 ml) was stirred with 5 g of 4A molecular sievesat 95° C. for 5 hours, while a gas was evolved. The mixture was cooled,diluted with EtOAc, filtered and the solvent evaporated. The crudeproduct was redissolved in EtOAc, washed with water, dried with MgSO4,and evaporated to give the isocyanate as a brown oil (700 mg)

Step 3

The isocyanate from step 2 (300 mg, 1.73 mmol) was dissolved in THF (3ml) and stirred with NaOH (2M, 2.4 ml) for 4 hours, then shaken betweenHCl (2M) and AcOEt. The aqueous phase was made basic with NaOH (conc.)and the product extracted into EtOAc, dried, and evaporated to give theamine (52 mg, 20%) as an oil.

Step 4

A solution of the amine from step 3 (110 mg, 0.748 mmol) indichloromethane was added slowly to a stirred solution of thiophosgene(0.063 ml, 0.823 mmol) in dichloromethane (1 ml) and 103 mg potassiumcarbonate in water (1 ml)at 0° C. After 15 min a cold solution of KOH(1.496 mmol) in water (1 ml) was added and the mixture shaken betweendichloromethane and water. The organic phase was dried and evaporated togive the isothiocyanate (90 mg) as an unstable oil.

Step 5

NaOH (2M, 0.237 ml) was added to a solution of 2-bromoethylaminehydrobromide (97 mg, 0.476 mmol) in water (0.1 ml) and stirred withether (0.5 ml) at 0° C. A solution of the isothiocyanate from step 4 (90mg, 0.476 mmol) in ether (1 ml) was added slowly and the mixture stirredat 0° C. for 30 minutes. The mixture was shaken between ether and water,and the ether phase extracted with HCl (2M). The aqueous phase was madebasic with NaOH (2M) and the product extracted into EtOAc, which wasdried and evaporated to yield 11 mg (10%) of the product. ¹H-NMR (300MHz CDCl₃) 1.68 (3H, s); 2.18 (1H, m); 2.73 (1H, m); 2.88 (1H, m); 3.03(1H, m); 3.22 (2H, t); 3.98 (2H, m); 7.27 (4H, m).

EXAMPLE 6

This Example illustrates the preparation of compound number 6.002.

Step 1.

Zinc dust (6 g) was washed with HCl (20% aq. 10 ml), then water, acetoneand ether, then added to a solution of 2-bromobenzaldehyde (7.03 ml,60.8 mmol) in THF (60 ml). Ethyl bromodifluoroacetate (9.5 ml, 73 mmol)in THF (30 ml) was added in portions. After the exothermic reaction wasover the mixture was stirred for 3 hours, then shaken between EtOAc,NH₄Cl (sat.) and NaCl (sat.). The organic phase was dried and evaporatedto yield the product (12 g) as a yellow oil.

Step 2.

A solution of the product from step 1 (12 g, 38.8 mmol) indichloromethane (30 ml) was added slowly to a solution of DAST indichloromethane (50 ml) at −70° C. After 30 minutes at this temperatureit was allowed to warm to room temperature and stirred for 2 hours, thencooled and poured onto cooled NaHCO₃ (1M). The product was extractedinto dichloromethane, dried and the solvent evaporated to yield theproduct (10 g) as a brown oil.

Step 3.

A solution of the product from step 2 (10 g, 32 mmol) in EtOH (200 ml)and NaOH (32%, 100 ml) was stirred at 90° C. for 5 hours, then cooledand shaken between ether and water. The aqueous phase was acidified withHCl (conc.) and the product extracted into ether, dried and evaporatedto yield the acid (3.2 g) as a brown oil.

Step 4

A solution of BuLi in hexane (1.6 M, 1.47 ml, 2.36 mmol) was addedslowly to a solution of the product from step 3 (304 mg, 1.07 mmol) at−10° C. After 10 minutes at this temperature it was warmed up to roomtemperature, poured onto HCl (2M aq.) and extracted into ether. Theether phase was dried and evaporated to yield 212 mg crude product,which was chromatographed on silica gel with 50% EtOAc/hexane to yieldthe 2,2,3-trifluoro-indanone (45 mg).

Step 5

A solution of 2,2,3-trifluoro-indanone (282 mg, 1.5 mmol), titaniumisopropoxide (0.886 ml, 2.99 mmol) and ammonia (2M in EtOH, 2.5 ml) inEtOH was stirred for 5 hours. The mixture was cooled to 0° C. and NaBH4(85 mg, 2.25 mmol) added. After stirring for 2 hours the mixture wasleft at room temperature overnight, then poured onto NH₄OH (25%, 10 ml)and extracted with EtOAc. The organic phase was washed with water,dried, and evaporated to yield the crude product (205 mg) as a brownoil. This was shaken between ether and HCl (2M aq.), basified with NaOH(2M) and extracted into ether. Evaporation yielded1-amino-2,2,3-trifluoro-indane (90 mg) as an oil.

Step 6

Chloroethylisothiocyanate (0.045 ml, 0.470 mmol) was added to a solutionof 1-amino-2,2,3-trifluoro-indane (80 mg, 0.427 mmol) in THF (0.5 ml).The white precipitate was filtered off to yield 40 mg of the product asan HCl salt. This was shaken between NaOH (aq.) and dichloromethane, theorganic phase dried and evaporated to yield 31 mg of the product. ¹H-NMR(300 MHz, CDCl₃) 3.39 (2H, t); 3.98 (2H, m); 5.44 (1H, t, J=8); 5.79(1H, ddd, J=49, 8, 6); 7.50 (4H, m).

EXAMPLE 7

This Example illustrates the preparation of compound number 6.002.

Step 1

A suspension of ammonium acetate (27.12 g, 351.8 mmol), malonic acid(18.31 g, 175.92 mmol) and 3,5-difluoro-benzaldehyde (25 g, 175.92 mmol)in ethanol (53 ml) was heated overnight under reflux, cooled to roomtemperature, the product filtered off, washed with ethanol and ether,and dried under vacuum to yield 21.07 g of product as a white powder.

Step 2.

TFAA (15 ml) was added to a solution of the product from step 1 (5 g,24.85 mmol) in TFA (15 ml). After 45 minutes the mixture was poured onto350 ml cold water and the product filtered off. It was washed with waterand dried overnight in the air to yield 6.06 g of the trifluoroacetateas white crystals.

Step 3

Sulfuric acid (0.036 ml, 0.67 mmol) was added to a solution of theproduct from step 2 (2.0 g, 6.78 mmol) in TFA (10 ml) and TFAA (10 ml),and the mixture heated for 4 hours under reflux. The solvent wasevaporated and the crude product stirred with ice/water (50 ml). Theproduct was filtered off and washed with water and dried under vacuum toyield the indanone (1.48 g) as beige crystals.

Step 4.

Sodium borohydride (712 mg, 18.8 mmol) was added in portions to asuspension of the product from step 3 (5 g, 17.9 mmol) in MeOH (50 ml)at 0° C. After 2 hours at 0° C. acetic acid (0.5 ml) and water (2 ml)was added and the solvent evaporated. The crude product was taken up indichloromethane, washed with HCl (1M) and NaHCO3 (sat.), dried andevaporated to give the product (4.87 g) as a mixture of cis and transisomers. This mixture was stirred with a little ether and the pure cisisomer filtered off, washed with ether and dried to yield 2.48 g.Chromatography of the mother liquors on silica with 5%MeOH/dichloromethane led to the pure trans isomer (537 mg) as whitecrystals.

Step 5.

A solution of the cis isomer from step 4 (600 mg, 2.13 mmol) andpotassium carbonate (1.47 g, 10.6 mmol) in methanol (20 ml) and water(4.5 ml) was heated under reflux for 2 hours, cooled and the solventevaporated. The crude product was shaken between NaOH (2M) anddichloromethane. The organic phase was dried and evaporated to yield 160mg product as brown crystals.

Step 6.

Chloroethylisothiocyanate (0.073 ml, 0.754 mmol) was added to a solutionof the product from step 5 (133 mg, 0.718 mmol) in THF (3 ml), and thesolution left overnight. The mixture was shaken between HCl (1M) andether, the aqueous phase was basified with NaOH (32%), and the productextracted into dichloromethane, which was then dried and evaporated. Thecrude product was washed with ether (1×2 ml, and 2×0.5 ml) to yield theproduct (105 mg) as beige crystals. m.p. 167° C.

EXAMPLE 8

This Example illustrates the preparation of compound number 1.003

(7-Chloro-1,2,3,4-tetrahydro-naphthalen-1-yl)-(4,5-dihydro-thiazol-2-yl)-amine

Titanium isopropoxide (710 mg, 0.74 mls, 2.5 mmol) is added to a mixtureof 7-chloro-1-tetralone (360 mg, 2 mmol) and 2-aminothiazoline (224 mg,2.2 mmol). The reaction mixture is stirred for 16 hours at roomtemperature, then diluted with dry methanol (5 ml). Excess sodiumborohydride is added carefully portionwise over a period of 45 minutes.The reaction mixture is stirred for a further 2 hours, then added to asaturated aqueous solution of Rochelle's salt and extracted withdichloromethane (2×25 mls). The organic phases are combined, washedsequentially with water and saturated brine, then filtered through a padof magnesium sulphate. The filtrate is concentrated under reducedpressure to give the crude product as a pale yellow gum. The crudeproduct is purified by column chromatography on silica, eluting withethyl acetate to give the title compound as a white solid Mp 164-6° C.Nmr data: (CDCl₃): 7.39 (1H, s, CH), 7.13 (1H, dd, CH), 7.01 (1H, s,CH), 4.90 (1H, m, CH), 4.06 (2H, m), 3.37 (2H, m), 2.72 (2H, m), 2.08(1H, m), 1.85 (3H, m)

EXAMPLE 9

This Example illustrates the preparation of compound number 1.014.

Step 1.

Hydroxylamine hydrochloride (590 mg, 8.4 mmol) was added in one portionto a stirring solution of ketone (1 g, 5.6 mmol) in methanol (15 ml) andthe resultant yellow solution was stirred at room temperature for 16hours. The reaction was then concentrated and triturated with ether andhexane to give a beige solid. This solid was collected and dried byfiltration and NMR and MS confirmed this to be the desired oxime (0.802g, 4.15 mmol, 74%).

Step 2.

Raney nickel (500 mg) was washed and added to a solution of oxime (532mg, 2.8 mmol) in methanolic ammonia (7M, 10 ml). This suspension wasthen subjected to 3.85 bar hydrogen pressure at room temperature for 2.5hours. The reaction was then filtered through hyflo and concentrated invacuo to a light green solid. This solid was found by NMR to be thedesired product (310 mg, 1.6 mmol, 57%) which was used crude in the nextstep.

Step 3.

1,1′-thiocarbonyldiimidazole (144 mg, 0.81 mmol) was added to a solutionof amine (145 mmol, 0.81 mmol, slight presence of nickel) in DMF andstirred at room temperature for 16 hours. Ethyl acetate and water werethen added and the organic phase washed with water and brine, dried(MgSO₄) and concentrated in vacuo. The crude orange oil was analysed byNMR, MS and IR, found to be desired isothiocyanate and was usedimmediately in the next step.

Step 4.

Triethylamine (0.15 ml, 1.1 mmol) was added to a suspension of2-chloroethylamine hydrochloride (130 mg, 1.1 mmol) in DCM and thesolution was stirred for 30 mins. Isothiocyanate (1.1 mmol) in DCM wasthen added. A GCMS was taken after an hour and showed the presence ofdesired product and SM. The reaction was stirred overnight. GCMS showedcomplete reaction and the solvent was removed in vacuo to give a crudeorange solid. This was recrystallised from ethanol to give the productas a white solid (crop 1, 31 mg, 0.117 mmol, 14%) and a second crop as abeige solid (21 mg, 0.08 mmol, 10%). Overall yield for two steps 24%.m.p. 234-235° C.

EXAMPLE 10

This Example illustrates the preparation of Compound No 8.017

A suspension of 0.70 g (3.2 mmol)(4,5-Dihydro-thiazol-2-yl)-indan-1-yl-amine, 0.52 g (4.8 mmol) cyanogenbromide and 1.56 g (4.8 mmol) CsCO₃ in 10 ml acetonitrile—was stirred at20° C. for 16 hours. The suspension was filtered and the solventevaporated. The crude product was purified by flash chromatography usingEtOAc/n-hexane (1:5) as eluent to yield 0.50 g of2-(Indan-1-ylimino)-thiazolidine-3-carbonitrile (white crystals, m.p.90-91° C.). ¹H-NMR (400 MHz, CDCl₃): 2.0-2.15 (1H, m); 2.40-2.50 (1H,m); 2.85-2.95 (1H, m); 3.0-3.10 (1H, m); 3.35-3.45 (2H, m), 3.90-4.0(2H, m), 4.65 (1H, t), 7.10-7.30 (4H, m).

EXAMPLE 11

This example illustrates the preparation of compound 2.006

Step 1.

15.0 g (102.6 mmol) 4-methyl-indan-1-one is dissolved in 125 ml MeOH.The solution is cooled to 0-5° C. and 4.3 g (112.9 mmol) NaBH₄ is addedportionwise while maintaining the temperature between 0-8° C. After theaddition of NaBH₄ the cool-bath is removed and the reaction mixture isstirred till TLC indicates completion of the reaction. The reactionmixture is poured into water and extracted three times with EtOAc. Thecollected organic layers are washed with water and brine, dried overMgSO₄ and filtered. After evaporation of EtOAc 4-methyl-indan-1-ol isisolated in 98% yield. The crude material may be used directly withoutfurther purification.

¹H-NMR (ppm, CDCl₃): 1.95-2.03 (m, 1H); 2.30 (s, 3H); 2.45-2.55 (m, 1H);2.70-2.80 (m, 1H); 2.95-3.05 (m, 1H); 5.25-5.30 (dd, 1H); 7.12 (d, 1H);7.18 (t, 1H); 7.28 (d, 1H).

Step 2.

4.34 g (29.28 mmol) 4-methyl-indan-1-ol and 7.8 ml (35.14 mmol)diphenylphosphoryl azide are dissolved in dry THF at room temperatureunder argon. To this mixture is added slowly 5.0 ml (35.14 mmol)1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction is stirred for 6 h atroom temperature (TLC monitoring). Then the mixture is poured into waterand extracted three times with toluene. The organic layers are combined,dried over MgSO₄ and concentrated in vacuo. Purification using silicagel chromatography (hexane/EtOAc 9:1) affords pure1-azido-4-methyl-indane as light orange liquid.

¹H-NMR (ppm, CDCl₃): 2.05-2.15 (m, 1H); 2.25 (s, 3H); 2.35-2.45 (m, 1H);2.72-3.02 (m, 1H); 4.82-4.88 (dd, 1H); 7.10 (d, 1H); 7.15 (t, 1H); 7.22(d, 1H).

Step 3.

1.0 g (5.8 mmol) 1-azido-4-methyl-indane is treated with 4.54 g (17.3mmol) triphenylphosphine in 26 ml THF and 1.4 ml H₂O at room temperatureovernight. Completion of the reaction is achieved by heating up themixture for additional 2.5 hours. The reaction mixture is then cooled toroom temperature and diluted with water. The pH is adjusted to 2 byadding cold (ca 0° C.) aqueous HCl (1M). After extraction with EtOAc theaqueous layer is separated, basified with NaOH (2M) and extracted intoEtOAc. The organic layer is then dried (MgSO₄) and concentrated in vacuoto give 4-methyl-indan-1-yl-amine as a light yellow liquid.

¹H-NMR (ppm, CDCl₃): 1.55 (br s, 1H); 1.60-1.70 (m, 1H); 2.25 (s, 3H);2.45-2.52 (m, 1H); 2.62-2.72 (m, 1H); 2.85-2.94 (m, 1H); 4.33 (t, 1H);6.98-7.05 (m, 1H); 7.10-7.15 (m, 2H).

Step 4.

A mixture of 0.36 ml (4.32 mmol) thiophosgene in 4 ml dichloromethane iscooled to 0° C. after which a cold (0° C.) solution of 0.5 g (3.60 mmol)K₂CO₃ in 4 ml water is added. The mixture is stirred for 10 min and 0.53g (3.60 mmol) indan-1-ylamine is then added drop wise with vigorousstirring at 0° C. After an additional 10 min a cold solution of 0.40 g(7.20 mmol) KOH in 4 ml water is added in one portion with cooling. Theorganic layer and three extracts (Et₂O) are combined, dried over MgSO₄,filtered and concentrated to give 1-isothiocyanato-4-methyl-indane as anorange brown liquid. The product is used directly without furtherpurification.

¹H-NMR (ppm, CDCl₃): 2.18-2.28 (m, 1H); 2.28 (s, 3H); 2.50-2.60 (m, 1H);2.75-2.85 (m, 1H); 2.95-3.05 (m, 1H); 5.19 (t, 1H), 7.11 (d, 1H); 7.18(t, 1H); 7.25 (d, 1H).

Step 5.

680 mg (3.59 mmol) 1-isothiocyanato-4-methyl-indane is dissolved in 13ml THF at room temperature under argon. Then 0.21 ml (3.59 mmol)2-amino-ethanol is added slowly. The reaction mixture is stirred at roomtemperature overnight. After completion of the reaction as indicated byTLC the solvent is removed under reduced pressure to give the crudeproduct. Subsequent purification by column chromatography on silica gel(CH₂Cl₂/MeOH 15:1) and stirring in Et₂O affords the title compound1-(2-hydroxy-ethyl)-3-(4-methyl-indan-1-yl)-thiourea as a white powder(Mp 90-93° C.).

¹H-NMR (ppm, CDCl₃): 1.85-1.95 (m, 1H); 2.25 (s, 3H); 2.55 (br s, 1H);2.60-2.70 (m, 1H); 2.71-2.81 (m, 1H); 2.86-2.99 (m, 1H); 3.62 (br s,2H); 3.78 (t, 2H); 5.67 (br s, 1H); 6.47 (br s, 1H), 6.11 (br s, 1H);7.07 (d, 1H); 7.12 (t, 1H); 7.18 (d, 1H).

Step 6.

500 mg (2.0 mmol) 1-(2-Hydroxy-ethyl)-3-(4-methyl-indan-1-yl)-thioureaand 786 mg (3.0 mmol) triphenylphosphine (TPP) were solved in 25 ml drytetrahydrofuran (THF) at room temperature under Argon. After 15 minutestirring at 20° C. a solution of 606 mg (3.0 mmol) disopropylazodicarboxylate (DIAD) in 10 ml THF was added drop wise whilemaintaining the temperature below 20° C. The reaction was complete after3 hours indicated by TLC. Then the reaction mixture was concentratedunder vacuo and 1 M HCl and ethyl acetate were added. The water layerwas separated and three times extracted with ethyl acetate. The ph ofthe water phase was then adjusted to ca 8-9 by adding solid NaOH. Thecrude product was extracted into CH₂Cl₂ and thoroughly washed with waterand brine. After drying over MgSO₄ and evaporation 428 mg(4,5-Dihydro-thiazol-2-yl)-(4-methyl-indan-1-yl)-amine were obtained asa white powder (Mp. 135-135° C.).

¹H-NMR (CDCl₃, ppm): 1.80-1.90 (m, 1H), 2.1.9 (s, 3H), 2.51-2.61 (m,1H), 2.61-2.72 (m, 1H), 2.80-2.90 (m, 1H), 3.30 (t, 2H), 3.92-4.05 (m,2H), 5.18 (t, 1H), 6.99 (d, 1H), 7.08 (t, 1H), 7.15 (d, 1H).

INTERMEDIATE EXAMPLE 1

This Example illustrates the preparation of 4,5-difluoro-1-indanamine.

Step 1 (According to G Toth et al. Synth. Comm. 1995, 25(19), 3067-74)

Triethylamine (30 ml) was added dropwise with stirring to formic acid(19 ml) at 0° C. To this solution was added 2,3-difluorobenzaldehyde (25g, 176 mmol) and Meldrum's acid (25.4 g, 176 mmol) and the mixtureheated at 100° C. for 2 hours, during which time gas evolved and 5 mldistillate was collected. The mixture was heated for a further 2 hours,then treated with ice/water (140 ml), and HCl (conc. aq.) to pH 1-2. Themixture was left at 5° C. overnight, and the product then filtered off,washed with water, dried first in the air then on the vacuum to yield29.11 g white crystals of the (2,3-difluoro)-3-propionic acid.

Step 2

Thionyl chloride (6.43 ml, 88.64 mmol) was added to a suspension of(2,3-difluoro)-3-propionic acid (15 g, 80.58 mmol) in DMF (0.17 ml) andhexane (60 ml) with stirring. After stirring for one hour at roomtemperature the brown solution was heated at 50° C. for 2 hours then thesolvent evaporated leaving the acid chloride as a brown oil. This wasdissolved in dichloromethane (60 ml), AlCl₃ was added in three portionswith stirring, and the dark brown/black mixture stirred overnight atroom temperature. The mixture was poured onto ice/water, acidified withHCl (conc. 15 ml) and the product extracted into dichloromethane, whichwas washed with HCl (2M) and NaOH (2M), dried (MgSO₄), and evaporated toyield 7.21 g 4,5-difluoro-1-indanone as a brown solid (m.p. 28-32° C.).

Step 3

4,5-difluoro-1-indanone (5.0 g, 35.68 mmol) and hydroxylaminehydrochloride (3.72 g, 53.52 mmol) were dissolved in pyridine (16 ml)and the dark brown solution left at room temperature overnight, thenpoured onto 40 ml of ice/water. The product was filtered off, washedwith water, and dried first in the air then under vacuum to yield 6.21 gof the oxime as a light beige powder.

Step 4

Sodium borohydride (4.34 g, 114.6 mmol) was added to a solution of TiCl₄(6.3 ml, 57.3 mmol) in DME (120 ml) at 0° C. under stirring. A gasevolved, the temperature rose to 20° C., and the solution became lightblue. After cooling to 0° C. a suspension of the oxime from step 3 (5.0g, 27.3 mmol) in DME (20 ml) was poured in. The temperature rose to 20°C. and the mixture was stirred at room temperature overnight. The darkblue suspension was added in portions to a mixture of potassium tartrate(200 mmol), water (100 ml), and NaOH (32%, 50 ml), which was stirred at0° C. This quenching was exothermic. After stirring for 2 hours theopalescent mixture was extracted with diethyl ether. The product wasthen extracted into HCl (1M), washed with ether, and after basifyingwith NaOH (32%), it was extracted into dichloromethane, which was driedand evaporated to yield 1.5 g of 4,5-difluoro-1-aminoindane as a lightbrown oil. ¹H-NMR (300 MHz, CDCl₃) 1.57 (3H, s, NH₂); 1.78 (1H, m); 2.57(1H, m); 2.81 (1H, m); 3.09 (1H, m); 4.37 (1H, t) 7.00 (2H, m).

INTERMEDIATE EXAMPLE 2

This Example illustrates the preparation of dimethyl-thiocarbamic acidO-(1-oxo-indan-4-yl) ester

13.3 g (87 mmol) 4-hydroxy-indan-1-one was added portion wise to asuspension of 2.3 g (91.3 mmol) NaH in 200 ml dry DMF and stirred at 20°C. After hydrogen evolution had ceased, a solution of 11.8 g (95.6 mmol)N,N′-dimethylthiocarbamoyl chloride in 50 ml dry DMF was slowly added.The resulting mixture was stirred overnight at 20° C. After completionof the reaction indicated by TLC the reaction mixture was poured intoice water and extracted several times with EtOAc. The organic extractwas thoroughly washed with 10% aq K2CO3, dried over MgSO4, andevaporated to dryness in vacuo. The crude product was purified by flashchromatography (hexane/EtOAc 3:1) to give 13.3 g (65%) ofdimethyl-thiocarbamic acid O-(1-oxo-indan-4-yl) ester as a slight yellowsolid compound. 1H-NMR (ppm, CDCl3): 2.65-2.7 (m, 2H), 3.05-3.1 (m, 2H),3.4 (s, 3H), 3.5 (s, 3H), 7.25 (d, 1H), 7.4 (t, 1H), 7.7 (d, 1H).

INTERMEDIATE EXAMPLE 3

This Example illustrates the preparation of4-difluoromethoxy-indan-1-one

10.0 g (76.5 mmol) 4-hydroxy-indan-1-one was added to a suspension of28.0 g (202 mmol) K₂CO₃ in 100 ml dry DMF and stirred overnight at 20°C. The suspension was heated to 85° C. and treated with 17.0 g (202mmol) gaseous CHClF2 for 45 minutes while maintaining the temperature at85° C. The resulting dark suspension was cooled to room temperature andpoured into 1500 ml water. The mixture was extracted with EtOAc. Afterseparation the organic layer was washed with water and brine, dried overMgSO₄ and evaporated to dryness. The crude product was purified by flashchromatography (hexane/EtOAc 9:1) to give 7.0 g (52%) of4-difluoro-methoxy-indan-1-one with mp 61-67° C.

1H-NMR (ppm, CDCl₃): 2.70-2.75 (m, 2H), 3.15-3.2 (m, 2H), 6.65 (t,broad, 1H) 7.35-7.45 (m, 2H), 7.65 (d, 1H).

INTERMEDIATE EXAMPLE 4

This Example illustrates the preparation of 2-p-tolyloxy-thiazoline

(according to Iwakura at al. J. Org. Chem. 1967, 32, 2362) Solid2-aminoethylbromide hydrobromide (6.57 g, 32.1 mmol) was added to asolution of para tolylchlorothionoformate (5 ml, 6.05 g, 32.1 mmol) intBuOMe (50 ml) with stirring at 0° C. NaOH (2M, 35 ml) was slowly addedcausing an exotherm to 29° C. After stirring at 0° C. for ca 30 minutes,NaOH (8M, ca 30 ml) was added to make the mixture basic. The product wasextracted into tBuOMe, washed with NaHCO₃ (1M) and NaCl (sat.), dried(MgSO₄) and evaporated to yield 5.125 g (83%) of the product as acolourless oil. ¹H-NMR (300 MHz, CDCl₃): 2.32 (3H, s, Me); 3.51 (2H, t,J=8); 4.06 (2H, t, J=8); 7.09 (2H, d, J=8); 7.18 (2H, d, J=8).

EXAMPLE 12

This Example illustrates the pesticidal/insecticidal properties ofcompounds of formula (I).

Test against were performed as follows:

Heliothis virescens (Tobacco Budworm):

Eggs (0-24 h old) were placed in 24-well microtiter plate on artificialdiet and treated with test solutions at an application rate of 200 ppmby pipetting. After an incubation period of 4 days, samples were checkedfor egg mortality, larval mortality, and growth regulation. Thefollowing compounds gave at least 80% control of Heliothis virescens:2.025, 2.024, 2.022, 2.001, 2.020, 2.031, 2.003, 2.019, 2.026, 7.010,2.030, 2.032, 1.007, 2.028, 2.040, 2.048, 2.049, 2.052, 2.058, 2.067,6.022, 6.023, 6.026, 6.027, 6.032, 6.035, 6.038, 8.017, 8.018, 8.025,8.031, 8.033, 8.034, 9.018, 9.019, 9.020, 10.001, 10.009, 10.011,10.013, 10.015, 10.017, 10.020, 10.022, 10.025, 12.008, 12.012, 12.017.

Myzus persicae (Green Peach Aphid):

Sunflower leaf discs were placed on agar in a 24-well microtiter plateand sprayed with test solutions at an application rate of 200/50/12.5ppm. After drying, the leaf discs were infested with an aphid populationof mixed ages. After an incubation period of 6 DAT, samples were checkedfor mortality.

The following compounds gave at least 80% control of Myzus persicae:2.025, 2.024, 2.022, 2.001, 7.006, 2.020, 2.031, 6.019, 4.001, 2.002,2.003, 2.006, 2.019, 2.016, 7.007, 2.026, 7.008, 2.014, 7.010, 2.030,1.012, 2.014, 2.031, 2.032, 2.052, 2.058, 2.066, 6.020, 6.022, 6.032,6.042, 8.017, 8.018, 8.030, 8.031, 8.032, 8.036, 9.001, 9.020, 10.002,10.012, 10.013, 10.014, 10.015, 10.019, 10.020, 10.021, 10.022, 10.025,12.008, 12.010, 12.011.

Myzus persicae (Green Peach Aphid):

Roots of pea seedlings, infested with an aphid population of mixed ages,were placed directly in the test solutions of 24 ppm. 6 days afterintroduction, samples were checked for mortality.

The following compounds gave at least 80% control of Myzus persicae:2.025, 2.024, 2.022, 2.001, 2.031, 4.001, 2.003, 2.006, 2.019, 2.030,2.058, 2.066, 2.067, 7.006, 8.025, 10.002, 10.006, 10.009, 10.011,10.015.

Tetranychus urticae (Two-Spotted Spider Mite):

Bean leaf discs on agar in 24-well microtiter plates wer sprayed withtest solutions at an application rate of 200/50/12.5 ppm. After drying,the leaf discs are infested with mite populations of mixed ages. 8 dayslater, discs are checked for egg mortality, larval mortality, and adultmortality.

The following compounds gave at least 80% control of Tetranychusurticae: 2.024, 2.022, 7.006, 2.020, 2.006, 2.019, 7.010, 2.030, 2.058,2.066, 2.067, 6.022, 6.032, 7.006, 8.018, 8.025, 8.026, 8.027, 8.031,8.032.

1. A compound of formula IC

wherein X is (i), (ii) or (iii)

Y is O, S(O)_(m), NR³, CR⁵R⁶, CR⁵R⁶—CR⁷R⁸, O—CR⁷R⁸, S(O)_(m)—CR⁷R⁸,NR³—CR⁷R⁸, CR⁵R⁶—O, CR⁵R⁶—S(O)_(m), CR⁵R⁶—NR³, SO₂—NR³, NR³—SO₂, NR³—Oor O—NR³; m is 0, 1, or 2; the ring (T)

is a 5- or 6-membered aromatic or heteroaromatic ring; R¹, R², R⁵, R⁶,R⁷ and R⁸ are each independently H, OH, halogen, nitro, cyano, rhodano,carboxy, formyl, formyloxy, G-, G-O—, G-S—, G-A-, R²¹R²²N—, R²¹R²²N-A-,G-O-A-, G-S-A-, G-A-O—, G-A-S—, G-A-NR²³—, R²¹R²²N-A-O—, R²¹R²²N-A-S—,R²¹R²²N-A-NR²³—, G-O-A-O—, G-O-A-S—, G-O-A-NR²³—, G-S-A-O, G-S-A-NR²³—,or R²⁰S(O)(═NR¹⁷)—, or two of the groups R¹, R², R⁵, R⁶, R⁷ and R⁸attached to the same carbon atom are ═O, ═S, ═NR¹¹ or ═CR¹²R¹³, or thegroups R¹ and R², R⁵ and R⁶ or R⁷ and R⁸ together with the carbon atomto which they are attached form a three to six membered ring, containingat least 2 carbon atoms and optionally containing one or two sulfurand/or one or two non-adjacent oxygen atoms or a group NR¹⁴, the ringbeing optionally substituted by C₁-C₆ alkyl; or two of the groups R¹,R², R⁵, R⁶, R⁷ and R⁸ attached to different atoms together with theatoms they are attached form a three to seven membered ring, thatoptionally contains one or two sulfur and/or one or two non-adjacentoxygen atoms or a group NR¹⁴, the ring being optionally substituted byC₁-C₆ alkyl or two of the groups R¹, R², R⁵, R⁶, R⁷ and R⁸ attached toadjacent atoms combine to form a bond; R¹⁰ is H, OH, cyano, formyl,tri(C₁-C₆ alkyl)silyl, G-, G-O—, G-S—, G-S—S—, G-A-, R²⁴R²⁵N—,R²⁴R²⁵N—S—, R²⁴R²⁵N-A-, R¹⁸N═C(R¹⁹)—, G-A-NR⁶⁹—, R⁷⁰R⁷¹C═N—, G-O-A- orG-S-A-, R¹¹ is H, OH, nitro, cyano, formyl, formyloxy, G-, G-O—, G-A-,R³⁶R³⁷N—, G-C(O)—O—, -G-C(O)—NR²⁶—, R³⁶R³⁷N—C(O)O—, G—OC(O)—,G-OC(O)—NR²⁶—; R¹² and R¹³ are each independently H, halogen, nitro,cyano, formyl, formyloxy, G-, G-O—, G-S—, G-A-, R⁴⁰R⁴¹N—, R⁴⁰R⁴¹N-A-,G-O-A-, G-A-O—, R⁴⁰R⁴¹N-A-O—, R⁴⁰R⁴¹N-A-S—, G-O-A-O—, G-O-A-S—,G-O-A-NR³⁰—, or R¹² and R¹³ together with the carbon atom to which theyare attached form a 3 to 6 membered carbocyclic ring; R³, R¹⁴, R¹⁵ andR¹⁶ are each independently H, OH, cyano, formyl, G-, G-O—, G-S—, G-A-,R²⁷R²⁸N—, R²⁷R²⁸N-A-, G-O-A-, G-S-A-, G-A-NR²⁹—, R²⁷R²⁸N-A-NR²⁹—,G-O-A-NR²⁹— or G-S-A-NR²⁹—; each R⁴ is independently OH, halogen, nitro,cyano, azido, rhodano, isothiocyanato, carboxy, formyl, formyloxy, G-,G-O—, G-S—, G-A-, R³¹R³²N—, R³¹R³²N-A-, G-O-A-, G-S-A-, G-A-O—, G-A-S—,G-A-NR³³—, R³¹R³²N-A-O—, R³¹R³²N-A-S—, R³¹R³²N-A-NR³³—, G-O-A-O—,G-O-A-S—, G-O-A-NR³³—, G-S-A-O, G-S-A-NR³³—, R²⁰S(O)(═NR¹⁷)—,R¹⁸N═C(R¹⁹)—, R⁴⁴R⁴⁵P(O)— or R⁴⁴R⁴⁵P(S)—, or 2 adjacent groups R⁴together with the carbon atoms to which they are attached form a 4, 5,6, or 7 membered carbocyclic or heterocyclic ring which may beoptionally substituted by halogen, or a group R⁴ together with a groupR³, R⁵ or R⁹ and the atoms to which they are attached form a 5-7membered ring optionally containing an NR¹⁵ group or an S or O atom, thering being optionally substituted by C₁-C₆ alkyl; n is 0, 1, 2, 3 or 4;R⁹ is H, formyl, G, G-A-, R³⁴R³⁵N-A-, G-O-A- or G-S-A-, or R⁹ togetherwith a group R¹, R⁵ or R⁷ and the atoms to which they are attached mayform a three to seven membered ring, that optionally may contain one ortwo sulfur and/or one or two non-adjacent oxygen atoms or a group NR¹⁶;R¹⁷ is H, G-, G-C(O)—, or G-OC(O)—; R¹⁸ is H, OH, cyano, nitro, G-, G-O—or R³⁸R³⁹N—; R¹⁹ is H, cyano, G-, G-O—, G-S— or R⁴²R⁴³N—; R²⁰ is C₁₋₆alkyl, optionally substituted phenyl, optionally substituted benzyl;each of the groups R²¹ to R⁴³ inclusive are independently H or G-, ortwo R²¹, R²², R²⁷, R²⁸, R³¹, R³², R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹, R⁴² orR⁴³ groups, together with the N atom to which they are attached, form agroup N═CR^(a)R^(b) (where R^(a) and R^(b) are H or C₁₋₆ alkyl) or twoR²¹, R²², R²⁴, R²⁵, R²⁷, R²⁸, R³¹, R³², R³⁴, R³⁵, R³⁶, R³⁷, R³⁸, R³⁹,R⁴² or R⁴³ groups, together with the N atom to which they are attached,form a five, six or seven-membered heterocyclic ring which may containone or two further heteroatoms selected from O, N or S and which may beoptionally substituted by one to four C₁₋₆ alkyl groups; R⁴⁴ and R⁴⁵ areindependently C₁₋₆alkyl, C₁₋₆-alkoxy, phenyl, phenoxy; G is optionallysubstituted C₁₋₁₂ alkyl, optionally substituted C₂₋₁₂ alkenyl,optionally substituted C₂₋₁₂ alkynyl, optionally substituted C₃₋₈cycloalkyl, optionally substituted C₃₋₈ cycloalkenyl, optionallysubstituted aryl, optionally substituted heteroaryl or optionallysubstituted heterocyclyl; R⁶⁹ is H, G-, G-C(O)—, or G-OC(O)—; R⁷⁰ andR⁷¹ are independently H, cyano, nitro, G-, G-O—, G-S—, or R⁷⁰ and R⁷¹together with the carbon atom to which they are attached form a five,six or seven-membered heterocyclic ring which may contain one or twofurther heteroatoms selected from O, N or S and which may be optionallysubstituted by one to four C₁₋₆ alkyl groups; A is S(O), SO₂, C(O) orC(S); or salts or N-oxides thereof, provided that the followingcompounds of the formulae (IC1) to (IC3) are excluded:

wherein R¹⁰⁰ is hydrogen or acetyl, and

wherein R¹⁰¹, R¹⁰², R¹⁰³ and R¹⁰⁴ are hydrogen, R²⁰⁰ and R³⁰⁰ areindependently of each other halogen, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₁₋₄alkylthio, trifluoromethyl or trifluoromethoxy, where s and t areindependently of each other 0, 1, 2 or 3, and the total of s+t is notgreater than
 3. 2. Compounds according to claim 1 of the formula ID

or salts or N-oxides thereof, wherein Y is CR⁵R⁶ or CR⁵R⁶CR⁷R⁸, and R¹,R², R⁴, R⁹, X and n are as defined in claim 1, where at least one of R¹,R², R⁴, R⁵, R⁶, R⁷, R⁸ or R⁹ is fluorine.
 3. Compounds according toclaim 1 of formula IE

or salts or N-oxides thereof, wherein Y is CR⁵R⁶, and R¹, R², R⁴, R⁹, Xare as defined in claim 1 and n is 0, 1, 2 or 3.